[ CAS No. 80-40-0 ] {[proInfo.proName]}

Name: 80-40-0|Ethyl 4-methylbenzenesulfonate|98%
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SKU: A216764
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DV 2D 3D

3d Animation Molecule Structure of 80-40-0

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Quality Control of [ 80-40-0 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 80-40-0 ]

SDS Specification

Alternatived Products of [ 80-40-0 ]

Product Details of [ 80-40-0 ]

CAS No. :	80-40-0	MDL No. :	MFCD00009100
Formula :	C₉H₁₂O₃S	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	VRZVPALEJCLXPR-UHFFFAOYSA-N
M.W :	200.25	Pubchem ID :	6638
Synonyms :	Ethyl p-toluenesulfonate

Calculated chemistry of [ 80-40-0 ] Expand+

Physicochemical Properties

Num. heavy atoms :	13
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.33
Num. rotatable bonds :	3
Num. H-bond acceptors :	3.0
Num. H-bond donors :	0.0
Molar Refractivity :	50.39
TPSA :	51.75 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-6.24 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.3
Log Po/w (XLOGP3) :	1.81
Log Po/w (WLOGP) :	2.8
Log Po/w (MLOGP) :	2.1
Log Po/w (SILICOS-IT) :	1.46
Consensus Log Po/w :	2.09

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	0.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-2.37
Solubility :	0.863 mg/ml ; 0.00431 mol/l
Class :	Soluble
Log S (Ali) :	-2.52
Solubility :	0.61 mg/ml ; 0.00305 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-3.25
Solubility :	0.113 mg/ml ; 0.000566 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	2.23

Safety of [ 80-40-0 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P305+P351+P338	UN#:	N/A
Hazard Statements:	H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 80-40-0 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Upstream synthesis route of [ 80-40-0 ]
Downstream synthetic route of [ 80-40-0 ]

[ 80-40-0 ] Synthesis Path-Upstream 1~6

1
[ 66224-66-6 ]
[ 80-40-0 ]
[ 2715-68-6 ]

Reference： [1] Journal of Organic Chemistry, 1980, vol. 45, # 20, p. 3969 - 3974

2
[ 80-40-0 ]
[ 105-53-3 ]
[ 601-75-2 ]

Reference： [1] Journal of the Chemical Society, 1928, p. 2304

3
[ 372-20-3 ]
[ 80-40-0 ]
[ 458-03-7 ]

Reference： [1] Bulletin of the Chemical Society of Japan, 2002, vol. 75, # 4, p. 789 - 800

4
[ 139-02-6 ]
[ 2785-29-7 ]
[ 80-40-0 ]
[ 767-90-8 ]
[ 103-73-1 ]

Reference： [1] Journal of the Chemical Society, 1912, vol. 101, p. 284

5
[ 2393-23-9 ]
[ 80-40-0 ]
[ 22993-76-6 ]
[ 125833-51-4 ]

Reference： [1] Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1972-1999), 1989, p. 1881 - 1886

6
[ 80-40-0 ]
[ 104-84-7 ]
[ 39099-13-3 ]

Reference： [1] Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1972-1999), 1989, p. 1881 - 1886

[ 80-40-0 ] Synthesis Path-Downstream 1~109

1
[ 2346-00-1 ]
[ 35080-47-8 ]
[ 80-40-0 ]
[ 21431-26-5 ]

Reference： [1]Patent: US2307916,1938,

2
[ 23012-10-4 ]
[ 80-40-0 ]
3-ethyl-2-methyl-oxazolium; toluene-4-sulfonate [ No CAS ]

Reference： [1]Journal of the Chemical Society,1952,p. 4823,4827, 2828

3
[ 91-63-4 ]
[ 5909-26-2 ]
[ 80-40-0 ]
(1-ethyl-[2]quinolyl)-(3-ethyl-2-methylsulfanyl-pyrimidin-4-yl)-methinium ; iodide [ No CAS ]

Reference： [1]Patent: GB425609,1933,

4
[ 491-35-0 ]
[ 13673-62-6 ]
[ 80-40-0 ]
(3-ethyl-benzoxazol-2-yl)-(1-ethyl-[4]quinolyl)-methinium ; iodide [ No CAS ]

Reference： [1]Journal of the Chemical Society,1939,p. 143,149

5
[ 95-21-6 ]
[ 13673-62-6 ]
[ 80-40-0 ]
[ 15185-40-7 ]

Reference： [1]Patent: US2310640,1934,

6
[ 120-75-2 ]
[ 5909-26-2 ]
[ 80-40-0 ]
(3-ethyl-benzothiazol-2-yl)-(3-ethyl-2-methylsulfanyl-pyrimidin-4-yl)-methinium ; iodide [ No CAS ]

Reference： [1]Patent: GB425609,1933,

7
[ 120-75-2 ]
[ 13673-62-6 ]
[ 80-40-0 ]
[ 68006-75-7 ]

Reference： [1]Patent: US2310640,1934,

8
[ 1198-37-4 ]
[ 2757-92-8 ]
[ 80-40-0 ]
(3-ethyl-benzothiazol-2-yl)-(1-ethyl-4-methyl-[2]quinolyl)-methinium ; iodide [ No CAS ]

Reference： [1]Journal of the Chemical Society,1949,p. 1503,1505

9
[ 700-46-9 ]
[ 615-22-5 ]
[ 80-40-0 ]
[ 112351-36-7 ]

Reference： [1]Patent: GB425609,1933,

10
[ 700-46-9 ]
[ 80-40-0 ]
[ 114697-17-5 ]

Reference： [1]Journal of the Chemical Society,1960,p. 5062 - 5072

11
[ 19219-98-8 ]
[ 13673-62-6 ]
[ 80-40-0 ]
(3-ethyl-benzoxazol-2-yl)-(3-ethyl-5,6-dimethyl-benzoxazol-2-yl)-methinium ; iodide [ No CAS ]

Reference： [1]Patent: US2310640,1934,

12
[ 85-02-9 ]
[ 80-40-0 ]
4-ethyl-4H-benzo[f]quinolin-3-one [ No CAS ]

Reference： [1]Journal of the Chemical Society,1931,p. 777,781

13
[ 55276-43-2 ]
[ 80-40-0 ]
[ 98433-26-2 ]

Reference： [1]Patent: DE828695,1950,
DRP/DRBP Org.Chem.,

14
[ 13673-62-6 ]
[ 5418-63-3 ]
[ 80-40-0 ]
(3-ethyl-benzoxazol-2-yl)-(1,3,3-trimethyl-3H-indol-2-yl)-methinium ; iodide [ No CAS ]

Reference： [1]Patent: US2310640,1934,

15
[ 1721-13-7 ]
[ 80-40-0 ]
[ 100247-56-1 ]

Reference： [1]Journal of the American Chemical Society,1959,vol. 81,p. 704,707

16
[ 2739-74-4 ]
[ 80-40-0 ]
[ 105837-99-8 ]

Reference： [1]Journal of the American Chemical Society,1959,vol. 81,p. 704,707

17
[ 101273-67-0 ]
[ 80-40-0 ]
[ 6780-49-0 ]
[(3-ethyl-5-phenoxy-4-phenyl-3H-thiazol-2-yliden)-ethyliden]-aniline; hydriodide [ No CAS ]

Reference： [1]Patent: US2743272,1952,

18
[ 855404-92-1 ]
[ 80-40-0 ]
[ 6780-49-0 ]
[3-ethyl-4-(4-methoxy-phenyl)-5-phenyl-3H-oxazol-2-yliden]-ethyliden}-aniline; toluene-4-sulfonate [ No CAS ]

Reference： [1]Journal of the Chemical Society,1952,p. 4823,4827, 2828

19
[ 2757-92-8 ]
[ 703-63-9 ]
[ 80-40-0 ]
(3-ethyl-benzothiazol-2-yl)-(1-ethyl-2-methyl-quinazolin-4-yl)-methinium ; iodide [ No CAS ]

Reference： [1]Patent: GB425609,1933,A

20
[ 90-05-1 ]
[ 80-40-0 ]
[ 17600-72-5 ]

Reference： [1]Annali di Chimica Applicata,vol. 15,p. 46
Chemisches Zentralblatt,1925,vol. 96,p. 2491

21
[ 64-17-5 ]
[ 98-59-9 ]
[ 80-40-0 ]

Yield	Reaction Conditions	Operation in experiment
90%	With pyridine; at 0℃; for 3h;	200 ml of a three-necked flask was placed in an ice-water bath at 0 C, 3.82 g (20 mmol) of p-toluenesulfonyl chloride and 50 mL of pyridine (dry) were added, and the mixture was stirred with 1.02 mL (20 mmol) of ethanol and reacted for 3 hours. After completion of the reaction, 100 mL of distilled water was added and extracted with dichloromethane (3 * 20 mL). The organic layer was washed twice with 6M HCl (2 * 30 mL) and washed successively with saturated NaHCO3 (30 mL) and 20% NaCl (30 mL) Once, separated. The organic layer was dried over anhydrous Na2SO4 for 8 h, filtered to remove anhydrous Na2SO4, and the organic liquid was evaporated to a final colorless oil Ethyl 4-methylbenzenesulfonate (yield 90%).
78%	With dmap; triethylamine; In dichloromethane; at 20℃; for 24h;Inert atmosphere;	To a solution of EtOH (590 mul, 10.0 mmol, 1.0 eq.) in CH2Cl2 (15 ml) were added TsCl (2.86 g, 15.0 mmol, 1.5 eq.), Et3N (2.1 ml, 15.0 mmol, 1.5 eq.) and DMAP (122 mg, 1.0 mmol, 0.1 eq.). After stirring for 24 h at rt under an atmosphere of argon, the mixture was washed with 1N HCl (10 ml), aq. sat. NaHCO3 (15 ml) and brine. The organic layer was dried over Na2SO4 and concentrated in vacuo to give a yellow liquid. Separation via column chromatography on silica gel (CyH/EtOAc 10:1 3:1) afforded the desired product (1.57 g, 7.8 mmol, 78%) as slightly yellow liquid.
	With dmap; triethylamine; In dichloromethane; at 0℃;	General procedure: To a solution of the suitable alcohol, phenol or amine (2 mmol) in dry DCM (10 mL), and cooled to 0 C, was added, portion-wise and drop-wise, 4-dimethylaminopyridine (0.4 mmol), p-toluenesulfonyl chloride (2.4 mmol) and triethylamine (3.00 mmol). The reaction mixture was stirred at 0 oC until TLC showed complete consumption of starting material. The resulting suspension was diluted with diethyl ether (25 mL), stirred for a further 30 min, and the precipitate removed by filtration. The solution was then washed sequentially with water (40 mL), 10% NaHCO3 (2x25 mL) and a saturated aqueous NaCl solution (10 mL). The combined organic layers were dried over MgSO4, filtered, concentrated in vacuo, and purified by column chromatography (CH2Cl2/hexane).

Reference： [1]Tetrahedron,2007,vol. 63,p. 5083 - 5087
[2]Patent: CN106631911,2017,A .Location in patent: Paragraph 0010
[3]Journal of Medicinal Chemistry,2010,vol. 53,p. 6228 - 6239
[4]Journal of Fluorine Chemistry,2016,vol. 182,p. 121 - 126
[5]Journal of Medicinal Chemistry,2014,vol. 57,p. 1236 - 1251
[6]Tetrahedron,1985,vol. 41,p. 3285 - 3296
[7]New Journal of Chemistry,2017,vol. 41,p. 4743 - 4746
[8]Organic Letters,2009,vol. 11,p. 1757 - 1759
[9]Journal of the Chemical Society. Perkin transactions II,1991,p. 1175 - 1179
[10]Monatshefte fur Chemie,1951,vol. 82,p. 452,455,460,464
[11]Journal of Organic Chemistry,1944,vol. 9,p. 235,238,239
[12]Journal of the Chemical Society,1925,vol. 127,p. 45
[13]Chemische Berichte,1925,vol. 58,p. 1322
[14]Justus Liebigs Annalen der Chemie,1903,vol. 327,p. 122
[15]Canadian Journal of Chemistry,1983,vol. 61,p. 2006 - 2009
[16]Canadian Journal of Chemistry,1983,vol. 61,p. 2466 - 2475
[17]Chemical Communications,1998,p. 2341 - 2342
[18]Tetrahedron Letters,1999,vol. 40,p. 2917 - 2918
[19]Journal of Medicinal Chemistry,2011,vol. 54,p. 7363 - 7374
[20]Chinese Chemical Letters,2012,vol. 23,p. 1115 - 1118,4
[21]Chinese Chemical Letters,2014,vol. 25,p. 1643 - 1647
[22]International Journal of Chemical Kinetics,2015,vol. 47,p. 744 - 750
[23]Arkivoc,2018,vol. 2018,p. 308 - 319

22
[ 110-52-1 ]
[ 3743-22-4 ]
[ 80-40-0 ]
[ 108696-20-4 ]

Reference： [1]Patent: DE828550,1950,
DRP/DRBP Org.Chem.,

23
[ 4869-59-4 ]
[ 80-40-0 ]
[ 5537-74-6 ]

Reference： [1]Journal of the Chemical Society,1928,p. 3004

24
[ 139-02-6 ]
[ 2785-29-7 ]
[ 80-40-0 ]
[ 767-90-8 ]
[ 103-73-1 ]

Reference： [1]Journal of the Chemical Society,1912,vol. 101,p. 284

25
[ 1004-22-4 ]
[ 80-40-0 ]
[ 622-76-4 ]

Reference： [1]Journal of the American Chemical Society,1938,vol. 60,p. 1882
[2]Annales de Chimie (Cachan, France),1931,vol. <10>16,p. 396
Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences,1930,vol. 191,p. 855
[3]Annales de Chimie (Cachan, France),1931,vol. <10>16,p. 396
Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences,1930,vol. 191,p. 855
[4]Journal of the American Chemical Society,1938,vol. 60,p. 1882
[5]Bulletin of the Chemical Society of Japan,1974,vol. 47,p. 2663 - 2671

26
[ 824-39-5 ]
[ 80-40-0 ]
[ 610-67-3 ]

Reference： [1]Yakugaku Zasshi/Journal of the Pharmaceutical Society of Japan,1951,vol. 71,p. 713
Chem.Abstr.,1952,p. 3976
[2]Yakugaku Zasshi/Journal of the Pharmaceutical Society of Japan,1951,vol. 71,p. 713
Chem.Abstr.,1952,p. 3976

27
[ 80-40-0 ]
[ 703-55-9 ]
[ 1127-76-0 ]

Reference： [1]Journal of the American Chemical Society,1925,vol. 47,p. 522

28
[ 80-40-0 ]
[ 105-53-3 ]
[ 601-75-2 ]

Reference： [1]Journal of the Chemical Society,1928,p. 2304

29
[ 80-40-0 ]
[ 110-81-6 ]

Reference： [1]Journal of the Iranian Chemical Society,2013,vol. 10,p. 201 - 205
[2]Monatshefte fur Chemie,1951,vol. 82,p. 970,974

30
[ 13673-62-6 ]
[ 80-40-0 ]
[ 20686-65-1 ]
(3-ethyl-benzoxazol-2-yl)-(3-ethyl-naphth[2,1-d]oxazol-2-yl)-methinium ; iodide [ No CAS ]

Reference： [1]Patent: US2310640,1934,

31
2-ethylmercapto-4H-benzo[d][1,3]thiazine [ No CAS ]
[ 80-40-0 ]
[ 20686-65-1 ]
3-ethyl-2-(4H-benzo[d][1,3]thiazin-2-ylmethylene)-2,3-dihydro-naphth[2,1-d]oxazole; hydriodide [ No CAS ]

Reference： [1]Journal of the Chemical Society,1945,p. 222,227

32
[ 80-40-0 ]
[ 20686-65-1 ]
[ 65087-24-3 ]

Reference： [1]Patent: US1939201,1932,

33
[ 13673-62-6 ]
[ 80-40-0 ]
[ 2682-45-3 ]
(3-ethyl-benzoxazol-2-yl)-(1-ethyl-naphtho[1,2-d]thiazol-2-yl)-methinium ; toluene-4-sulfonate [ No CAS ]

Reference： [1]Patent: US2310640,1934,

34
[ 119600-44-1 ]
[ 80-40-0 ]
[ 2682-45-3 ]
[ 143118-10-9 ]

Reference： [1]Journal of the Chemical Society,1949,p. 1503,1505

35
[ 51741-78-7 ]
[ 80-40-0 ]
[ 2682-45-3 ]
1-(1-ethyl-naphtho[1,2-d]thiazol-2-yl)-3-(3-methyl-benzothiazol-2-yl)-2-methyl(?)mercapto trimethinium ; iodide [ No CAS ]

Reference： [1]Patent: US2397013,1942,

36
[ 80-40-0 ]
[ 2682-45-3 ]
[ 42952-29-4 ]

Reference： [1]Journal of the American Chemical Society,2016,vol. 138,p. 10112 - 10115
[2]Journal of the American Chemical Society,1935,vol. 57,p. 547,550

37
[ 80-40-0 ]
[ 538-09-0 ]
[ 1748-08-9 ]

Reference： [1]Journal of the Chemical Society,1956,p. 1411,1416

38
[ 80-40-0 ]
[ 69-89-6 ]
[ 31542-50-4 ]

Reference： [1]Anales des la Asociacion Quimica Argentina,1957,vol. 45,p. 79,82

39
[ 254-60-4 ]
[ 64-17-5 ]
[ 98-59-9 ]
[ 80-40-0 ]

Reference： [1]Canadian Journal of Chemistry,1986,vol. 64,p. 1184 - 1188

40
[ 2047-89-4 ]
[ 80-40-0 ]
5-Ethyl-5,6,7,8,9,10-hexahydro-cyclohepta[b]indole [ No CAS ]

Reference： [1]Journal of the Chemical Society. Perkin transactions I,1984,p. 2297 - 2304

41
[ 818-38-2 ]
[ 6192-52-5 ]
[ 80-40-0 ]

Reference： [1]Chemical and pharmaceutical bulletin,1985,vol. 33,p. 1380 - 1386

42
[ 1047-16-1 ]
[ 80-40-0 ]
[ 99762-78-4 ]

Reference： [1]Chemistry of Heterocyclic Compounds,1985,vol. 21,p. 792 - 795
Khimiya Geterotsiklicheskikh Soedinenii,1985,p. 952 - 955

43
[ 120-73-0 ]
[ 80-40-0 ]
[ 5427-23-6 ]

Reference： [1]Journal of Organic Chemistry,1980,vol. 45,p. 3969 - 3974

44
[ 106-47-8 ]
[ 80-40-0 ]
[ 7255-72-3 ]
[ 13519-75-0 ]

Reference： [1]Journal of the Chemical Society. Perkin transactions II,1989,p. 1881 - 1886

45
[ 104-86-9 ]
[ 80-40-0 ]
[ 69957-83-1 ]
Toluene-4-sulfonic acid; compound with 4-chloro-benzylamine [ No CAS ]

Reference： [1]Journal of the Chemical Society. Perkin transactions II,1989,p. 1881 - 1886

46
[ 2393-23-9 ]
[ 80-40-0 ]
[ 22993-76-6 ]
[ 125833-51-4 ]

Reference： [1]Journal of the Chemical Society. Perkin transactions II,1989,p. 1881 - 1886

47
[ 383-62-0 ]
[ 68-12-2 ]
[ 80-40-0 ]
[ 141546-96-5 ]

Reference： [1]Journal of the Chemical Society. Chemical communications,1992,p. 540 - 541

48
[ 66224-66-6 ]
[ 80-40-0 ]
[ 2715-68-6 ]

Reference： [1]Journal of Organic Chemistry,1980,vol. 45,p. 3969 - 3974

49
[ 157432-87-6 ]
[ 80-40-0 ]
[ 125065-64-7 ]

Reference： [1]Journal of the American Chemical Society,1990,vol. 112,p. 6979 - 6985
[2]Tetrahedron Letters,1989,vol. 30,p. 2681 - 2684

50
[ 117570-63-5 ]
[ 80-40-0 ]
[ 117570-62-4 ]

Reference： [1]Journal of Medicinal Chemistry,1990,vol. 33,p. 1375 - 1379

51
[ 80-40-0 ]
[ 104-84-7 ]
[ 39099-13-3 ]
Toluene-4-sulfonic acid; compound with 4-methyl-benzylamine [ No CAS ]

Reference： [1]Journal of the Chemical Society. Perkin transactions II,1989,p. 1881 - 1886

52
[ 81475-22-1 ]
[ 80-40-0 ]
5,11,17,23,29-penta-tert-butyl-31,32,33,34,35-pentaethoxycalix<5>arene [ No CAS ]

Reference： [1]Journal of the American Chemical Society,1995,vol. 117,p. 586 - 596

53
[ 31729-66-5 ]
[ 80-40-0 ]
[ 1010-24-8 ]

Reference： [1]Journal of Organic Chemistry,1965,vol. 30,p. 23 - 28

54
[ 3484-18-2 ]
[ 80-40-0 ]
[ 174274-96-5 ]

Reference： [1]Journal of Medicinal Chemistry,1996,vol. 39,p. 892 - 903

55
[ 80-40-0 ]
[ 2682-45-3 ]
6-methyl-2-methylsulfanyl-benzoxazole [ No CAS ]
(3-ethyl-6-methyl-benzoxazol-2-yl)-(1-ethyl-naphtho[1,2-d]thiazol-2-yl)-methinium ; toluene-4-sulfonate [ No CAS ]

Reference： [1]Patent: US2310640,1934,

56
[ 372-20-3 ]
[ 80-40-0 ]
[ 458-03-7 ]

Reference： [1]Bulletin of the Chemical Society of Japan,2002,vol. 75,p. 789 - 800

57
[ 69358-30-1 ]
[ 80-40-0 ]
[ 890709-71-4 ]

Reference： [1]Organic Letters,2006,vol. 8,p. 2103 - 2106

58
[ 115084-80-5 ]
[ 80-40-0 ]
[ 890709-69-0 ]

Reference： [1]Organic Letters,2006,vol. 8,p. 2103 - 2106

59
[ 80-40-0 ]
[ 151004-17-0 ]
[ 890709-68-9 ]

Reference： [1]Organic Letters,2006,vol. 8,p. 2103 - 2106

60
[ 80-40-0 ]
[ 53618-00-1 ]
[ 890709-70-3 ]

Reference： [1]Organic Letters,2006,vol. 8,p. 2103 - 2106

61
[ 90-66-4 ]
[ 80-40-0 ]
2-tert-butyl-6-[(3-tert-butyl-2-ethoxy-5-methylphenyl)thio]-4-methylphenol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
52%		A 100 mL Schlenk flask was charged with a stirbar, 4.010 g 2,2'-thiobis(6-tert-butyl4-methylphenol) (BPS-1, 11.2 mmol), 25 mL dry toluene, and 0.283 g sodium hydride (11.8 mmol). The thick whitish paste was stirred at ambient temperature for 1.5 hours, then placed in an oil bath set at 130 C. and refluxed for 2 hours. The flask was then removed from heat and allowed to cool. A solution of 2.250 g ethyl p-toluenesulfonate (11.2 mmol) in 15 mL dry toluene was added via cannula into the slurry of deprotonated BPS-1. The flask was returned to the oil bath, where the thick blue-green slurry was allowed to reflux with agitation for another hour, and then allowed to cool slowly overnight. The contents of the flask were then filtered and washed with toluene. Solvent was then removed in vacuo. The desired monoether was separated from small amounts of starting material and diether by column chromatography with a hexanes/methylene chloride solution at a volume ratio of 7:1. A total of 2.264 g BPS-1-Et was recovered (52%). The proton NMR spectrum is similar to that described in Example 4.
50%		Under N2, a 250 mL 3-necked round-bottom flask was charged with stirbar, 10.036 g 2,2'-thiobis(6-tert-butyl-4-methylphenol) (28.0 mmol), and 100 mL THF. To this solution was added 0.685 g sodium hydride (28.5 mmol, 1.02 eq.). An addition funnel and reflux condenser with vacuum adapter were attached and the apparatus placed under N2 bubbler and immersed in an oil bath. The oil bath temperature was raised and the mixture refluxed for 2 hours. While the reaction mixture was still refluxing, a solution of 5.595 g ethyl p-toluenesulfonate (27.9 mmol, 1 eq.) was added over a period of 3 hours. (During this period, an additional 50 mL THF were injected into the flask to make up for solvent apparently lost to a leaky joint.) The thick blue-green slurry with white precipitate was refluxed overnight. Next, the slurry was quenched with 200 mL water and mixed with 200 mL diethyl ether to extract the reaction product. The aqueous phase was washed with a further 50 mL of diethyl ether. The combined organic fractions were dried over anhydrous sodium sulfate, filtered, and reduced to a viscous yellow fluid by rotary evaporation. The material was purified first by column chromatography in hexanes/toluene at a volume ratio of 40:1, with one less-pure fraction recrystallized from ethanol. Three crops were recovered, with a total weight of 5.36 g (50%). [0123] 1H NMR (CDCl3), delta (ppm): 7.22 (d, J=2.0 Hz), 1H, Ar-H; 7.17 (s), 1H, OH; 7.11 (d, J=2.0 Hz), 1H, Ar-H; 6.93 (d, J=2.0 Hz), 1H, Ar-H; 6.50 (d, J=2.0), 1H, Ar-H; 4.15 (q, J=7.0 Hz), 2H, CH2CH3; 2.24 (s), 3H, Ar-CH3; 2.12 (s), Ar-CH3; 1.52 (t, J=7.0 Hz), CH2CH3; 1.36 (s), t-Bu.

Reference： [1]Patent: US2004/142814,2004,A1 .Location in patent: Page/Page column 7-8
[2]Macromolecules,2005,vol. 38,p. 322 - 333
[3]Patent: US2004/142814,2004,A1 .Location in patent: Page/Page column 7

62
[ 879491-32-4 ]
[ 80-40-0 ]
[ 879491-33-5 ]

Yield	Reaction Conditions	Operation in experiment
51%	With sodium hexamethyldisilazane; In tetrahydrofuran; at -78 - 0℃; for 1.16667h;	2-{4-[2-Ethoxy-3-(4-trifluoromethyl-phenoxy)-propylsulfanyl]-2-meth yl-phenoxy}-2-methyl-propionic acid ethyl ester To a solution of E1 (148 mg, 0.313 mmol) in anhydrous THF (1 mL) at -78 C. was added NaHMDS (1 M in THF, 0.313 mL, 0.313 mmol) and EtOTs (55.8 mg, 0.313 mmol). After stirring 10 minutes, the solution was then allowed to warm to 0 C. and continue stirring at 0 C. for one hour. Ether was added and the solution was washed with water and then saturated saline. After dry over Na2SO4 and concentration, the crude product was purified by column chromatography (EtOAc:hexanes=20:1) to give 80 mg (51%) of compound E2; 1H NMR (300 MHz, CDCl3) delta 7.52 (d, J=8.6 Hz, 2H), 7.21 (d, J=2.0 Hz, 1H), 7.11 (dd, J=8.5, 2.3 Hz, 1H), 6.93 (d, J=8.6 Hz, 2H), 6.56 (d, J=8.5 Hz, 1H), 4.23 (q, J=7.1 Hz, 2H), 4.17-4.08 (m, 2H), 3.76 (m, 2H), 3.60 (q, J=6.9 Hz, 2H), 3.11 (d, J=5.7 Hz, 2H), 2.16 (s, 3H), 1.57 (s, 6H), 1.24 (t, J=7.1 Hz, 3H), 1.18 (t, J=7.0 Hz, 3H); MS (ES) m/z: 523 (M+Na+).

Reference： [1]Patent: US2006/58393,2006,A1 .Location in patent: Page/Page column 27

63
[ 459818-00-9 ]
[ 80-40-0 ]
[ 459817-28-8 ]

Yield	Reaction Conditions	Operation in experiment
74%	With potassium carbonate; In N,N-dimethyl-formamide;	c 3-Ethoxy-7-methyl-1H-indole-2-carboxylic acid ethyl ester Toluene-4-sulfonic acid ethyl ester (274 mg, 1.37 mmol) and potassium carbonate (378 mg, 2.74 mmol) were added to a solution of 3-hydroxy-7-methyl-1H-indole-2-carboxylic acid ethyl ester (300 mg, 1.37 mmol) in N,N-dimethylformamide (3 mL). The mixture was stirred at 50 C. for 16 h, then cooled to room temperature and partitioned between ethyl acetate and water. The organic layer was separated, washed with brine, dried (MgSO4), and evaporated. Chromatography (SiO2, hexane/ethyl acetate 6:1) afforded the title compound (250 mg, 74%). White solid, ISP-MS: m/e=248.2 ([M+H+]).

Reference： [1]Patent: US2002/169163,2002,A1

64
[ 118511-81-2 ]
[ 80-40-0 ]
[ 170364-85-9 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate; In ethanol;	PREPARATION 3 1-(1-Ethyl-piperidin-4-yl)-1H-indole To a solution of <strong>[118511-81-2]1-piperidin-4-yl-1H-indol</strong>e (0.6 g, 3 mmol) in 5 mL of dry ethanol was added anhydrous potassium carbonate (680 mg, 4.9 mmol). After stirring for 15 minutes at ambient temperature, ethyl p-toluenesulfonate (0.48 mL,4.5 mmol) was added. The reaction was heated under reflux for 24 hours with stirring, quenched with water, extracted with methylene chloride (2*), dried and evaporated to give a residue. The residue was chromatographed on silica gel with toluene/acetone (50:50) to yield 360 mg straw colored material (53% of theory).

Reference： [1]Patent: US5545636,1996,A

65
[ 80-40-0 ]
[ 62749-33-1 ]
[ 62749-38-6 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate; In N-methyl-acetamide; water;	C-5. 1-Ethyl-3-nitro-5-(4-pyridinyl)-2(1H)-pyridinone -- A mixture containing 21.7 g. of 3-nitro-5-(4-pyridinyl)-2(1H)-pyridinone, 13.8 g. of anhydrous potassium carbonate and 400 ml. of dry dimethylformamide was stirred at room temperature for one hour on a steam bath for one hour and then allowed to cool to room temperature. To the stirred yellow suspension was added a solution containing 20 g. of <strong>[80-40-0]ethyl tosylate</strong> in 10 ml. of dimethylformamide and the resulting mixture was stirred at room temperature overnight (about fifteen hours) and then on a steam bath for ninety minutes. The mixture was cooled and filtered. The filtrate was concentrated to near dryness under reduced pressure and 400 ml. of water was added. The yellow solid was collected by filtration, washed with water and dried at 50 C. in vacuo for eighteen hours to yield 5.5 g. of pale yellow needles, m.p. 124-126 C. (see below for recrystallization and identification). The filtrate was stored at 0 C. and the resulting yellow crystalline precipitate was collected and dried at 100 C. and 10 mm. for four hours to yield 8.0 g. of the product, 1-ethyl-3-nitro-5-(4-pyridinyl)-2(1H)-pyridinone, m.p. 175-176 C. A sample of this product was recrystallized from 95% ethanol to produce the yellow crystalline 1-ethyl compound, m.p. 175-176 C., whose nuclear magnetic resonance spectrum (10% in CF3 COOD) is consistent with the assigned N-ethyl structure. A portion of the above-noted pale yellow needles melting at 124-126 C. was recrystallized from ethanol-water (3/1, v/v) to yield white needles, m.p. 126-127 C., which was identified by its nuclear magnetic resonance spectrum (10% in CF3 COOD) as 2-ethoxy-3-nitro-5-(4-pyridinyl)pyridine.
	With potassium carbonate; In N-methyl-acetamide; water;	C-5. 1-Ethyl-3-nitro-5-(4-pyridinyl)-2(1H)-pyridinone -- A mixture containing 21.7 g. of 3-nitro-5-(4-pyridinyl)-2(1H)-pyridinone, 13.8 g. of anhydrous potassium carbonate and 400 ml. of dry dimethylformamide was stirred at room temperature for 1 hour on a steam bath for 1 hour and then allowed to cool to room temperature. To the stirred yellow suspension was added a solution containing 20 g. of <strong>[80-40-0]ethyl tosylate</strong> in 10 ml. of dimethylformamide and the resulting mixture was stirred at room temperature overnight (about 15 hours) and then on a steam bath for ninety minutes. The mixture was cooled and filtered. The filtrate was concentrated to near dryness under reduced pressure and 400 ml. of water was added,. The yellow solid was collected by filtration, washed with water and dried at 50 C. in vacuo for 18 hours to yield 5.5 g. of pale yellow needles, m.p. 124-126 C. (see below for recrystallization and identification). The filtrate was stored at 0 C. and the resulting yellow crystalline precipitate was collected and dried at 100 C. and 10 mm. for four hours to yield 8.0 g. of the product, 1-ethyl-3-nitro-5-(4-pyridinyl)-2(1H)-pyridinone, m.p. 175-176 C. A sample of this product was recrystallized from 95% ethanol to produce the yellow crystalline 1-ethyl compound, m.p. 175-176 C., whose nuclear magnetic resonance spectrum (10% in CF3 COOD) is consistent with the assigned N-ethyl structure. A portion of the above-noted pale yellow needles melting at 124-126 C. was recrystallized from ethanol-water (3/1, v/v) to yield white needles, m.p. 126-127 C., which was identified by its nuclear magnetic resonance spectrum (10% in CF3 COOD) as 2-ethoxy-3-nitro-5-(4-pyridinyl)pyridine.
	With potassium carbonate; In N-methyl-acetamide; water;	C-5. 1-Ethyl-3-nitro-5-(4-pyridinyl)-2(1H)-pyridinone A mixture containing 21.7 g. of 3-nitro-5-(4-pyridinyl)-2(1H)-pyridinone, 13.8 g. of anhydrous potassium carbonate and 400 ml. of dry dimethylformamide was stirred at room temperature for 1 hour on a steam bath for 1 hour and then allowed to cool to room temperature. To the stirred yellow suspension was added a solution containing 20 g. of <strong>[80-40-0]ethyl tosylate</strong> in 10 ml. of dimethylformamide and the resulting mixture was stirred at room temperature overnight (about 15 hours) and then on a steam bath for 90 minutes. The mixture was cooled and filtered. The filtrate was concentrated to near dryness under reduced pressure and 400 ml. of water was added. The yellow solid was collected by filtration, washed with water and dried at 50 C. in vacuo for 18 hours to yield 5.5 g. of pale yellow needles, m.p. 124-126 C. (see below for recrystallization and identification). The filtrate was stored at 0 C. and the resulting yellow crystalline precipitate was collected and dried at 100 C. and 10 mm. for 4 hours to yield 8.0 g. of the product, 1-ethyl-3-nitro-5-(4-pyridinyl)-2(1H)-pyridinone, m.p. 175-176 C. A sample of this product was recrystallized from 95% ethanol to produce the yellow crystalline 1-ethyl compound, m.p. 175-176 C., whose nuclear magnetic resonance spectrum (10% in CF3 COOD) is consistent with the assigned N-ethyl structure. A portion of the above-noted pale yellow needles melting at 124-126 C. was recrystallized from ethanol-water (3/1, v/v) to yield white needles, m.p. 126-127 C., which was identified by its nuclear magnetic resonance spectrum (10% in CF3 COOD) as 2-ethoxy-3-nitro-5-(4-pyridinyl)pyridine.

Reference： [1]Patent: US4072746,1978,A
[2]Patent: US4107315,1978,A
[3]Patent: US4004012,1977,A

66
(cis-(3-hydroxy)cyclopentyl)diphenylacetonitrile [ No CAS ]
[ 80-40-0 ]
para-toluenesulfonic acid (trans-3-(cyano(diphenyl)methyl)cyclopentyl) ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
70%	With triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; at -10 - 20℃; for 16h;	A solution of (cis-(3-hydroxy)cyclopentyl)diphenylacetonitrile (15.4 g, 55.6 mmol) obtained in Reference Example 2, triphenylphosphine (21.0 g, 80.1 mmol), and para-toluenesulfonic acid ethyl ester (12.1 ml, 80.1 mmol) in tetrahydrofuran (240 ml) was added dropwise with azodicarboxylic acid diethyl ester (14.5 ml, 92.4 mmol) at - 10C under an argon atmosphere, and the mixture was stirred at a temperature below 0C for 2 hours, and then stirred at room temperature for 14 hour. The reaction mixture was concentrated under reduced pressure, and the resulting residue was purified by silica gel column chromatography (developing solvent: toluene) to obtain oil. The resulting oil was added with isopropyl ether and crystallized to obtain 16.7 g (yield: 70%) of the title compound as white crystalline powder. 1H-NMR (CDCl3, delta PPM): 1.56-2.14 (6H, m), 2.43 (3H, s), 3.28-3.52 (1H, m), 4.88-5.06 (1H, m), 7.10-7.54 (12H, m), 7.76 (2H, brd, J=8.25Hz)

Reference： [1]Patent: EP1939183,2008,A1 .Location in patent: Page/Page column 15-16

67
(cis-(3-hydroxy)cyclopentyl)diphenylacetonitrile [ No CAS ]
[ 80-40-0 ]
para-toluenesulfonic acid (cis-3-(cyano(diphenyl)methyl)cyclopentyl) ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
74%	In pyridine; at 20℃; for 6h;	A solution.of (cis-(3-hydroxy)cyclopentyl)diphenylacetonitrile (27.7 g, 100 mmol) obtained in Reference Example 2 and para-toluenesulfonyl chloride (23 g, 120 mmol) in pyridine (100 ml) was stirred at room temperature for 6 hours. The reaction mixture was added with water, and extracted with ethyl acetate, and the organic layer was washed with 1 N hydrochloric acid, and then dried over anhydrous magnesium sulfate. The organic layer was filtered, and then concentrated under reduced pressure, and the resulting powder was washed with a mixed solvent ethyl acetate/isopropyl ether to obtain 32.0 g (yield: 74%) of the title compound. 1H-NMR (CDCl3, delta PPM): 1.58-2.09 (6H, m), 2.42 (3H, s), 2.90-3.06 (1H, m), 4.88-5.01 (1H, m), 7.16-7.44 (12H, m), 7.77 (2H, d, J=8.3Hz).

Reference： [1]Patent: EP1939183,2008,A1 .Location in patent: Page/Page column 22

68
[ 25981-82-2 ]
2,5-bis[(phenylamino)methylene]cyclopentylidene diphenylaminium tetrafluoroborate [ No CAS ]
[ 80-40-0 ]
BF₄^(1-)*C₄₇H₅₂N₃⁽¹⁺⁾ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
80%		<Formation of image recording layer>; [Preparation of compound having a specific structure (A-1)]; 10.13 g of <strong>[80-40-0]ethyl tosylate</strong> and 8.7 g of 2,3,3,5-tetramethyl-3H-indole were blended at 120C for 2 hours and cooled to room temperature 13.2 g of 2,5-bis[(phenylamino)methylene]cyclopentylidene diphenylaminium tetrafluoroborate, 5.06 g of acetic anhydride, 12.6 g of triethylamine, and 500 ml of 2-propanol were added thereto, and the mixture was stirred at 80C additionally for 3 hours. The mixture was allowed to cool to room temperature. The crystal precipitated was collected by filteration, and was washed sufficiently with water, to give 14.9 g of a cyanine colorant (IR-1) (yield: 80%). 10.0 g of the cyanine colorant (IR-1) obtained was dissolved in 100 ml of chloroform, and 6.0 g of manganese dioxide was added. The mixture was stirred at room temperature for 48 hours. Manganese dioxide was filtered off, the crude crystal obtained after distillation of chloroform was resuspended in 50 ml of ethyl acetate, to give 9.5 g of a compound (A-1) (yield: 95%). The preparative scheme is shown below.

Reference： [1]Patent: EP1849836,2007,A2 .Location in patent: Page/Page column 73

69
[ 1044517-73-8 ]
[ 80-40-0 ]
[ 1044517-71-6 ]

Reference： [1]Journal of Medicinal Chemistry,2008,vol. 51,p. 4404 - 4411

70
[ 1120-24-7 ]
[ 107-14-2 ]
[ 80-40-0 ]
(cyanomethyl)dimethyldecylammonium tosylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
93%		Example 7 Synthesis of (cyanomethyl)dimethyldecylammonium Tosylate 185.35 g (1 mol) of dimethyldecylamine were initially charged at 50 C. in 1000 ml of butyl acetate, and 75.5 g (1 mol) of chloroacetonitrile were added. The reaction mixture was stirred at 60 C. for 6 hours. Then 200.26 g (1 mol) of ethyl para-toluenesulfonate were added and the reaction mixture was stirred at 80 C. for 90 minutes, in the course of which vigorous evolution of gas was observed. The reaction mixture was cooled slowly to 5 C., and the precipitated solid was washed twice with 50 ml each time of butyl acetate and dried at 60 C. under reduced pressure. 368.78 g (0.93 mol) of (cyanomethyl)dimethyldecylammonium tosylate were obtained as a colorless solid, corresponding to a yield of 93%. 1H NMR (D2O): delta=7.70 (2H, d); delta=7.37 (2H, d); delta=4.75 (2H, s); delta=3.56 (2H, m); delta=3.33 (6H, s); delta=2.40 (3H, s); delta=1.85 (2H, m); delta=1.43-1.25 (14H, m); delta=0.89 (3H, t).

Reference： [1]Patent: US2009/149668,2009,A1 .Location in patent: Page/Page column 4

71
[ 616-47-7 ]
[ 80-40-0 ]
1-ethyl-3-methylimidazolium p-toluenesulfonate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
98%	In neat (no solvent); at 20℃; for 0.5h;	An agate mortar was charged with dry K2CO3 (5 g), tetraethylene glycol (10 mmol, 1.72 mL), TsCl (24 mmol, 4.57 g) and grinded for 5 min. Upon reaction completion, monitored by TLC (CCl4/EtOAc, 4:1, v/v), the excess of TsCl was removed by wetting the reaction mixture with drops of t-BuOH and irradiating in a domestic microwave oven for 2 min. The prepared tetraethylene glycol ditosylate, was isolated by extraction with ether (3× 10 mL). Then, 1-methylimidazole (25 mmol, 2 mL) was added to the tetraethylene glycol ditosylate (10 mmol, 4.74 g) and allowed to stir at r.t. for 30 min. The work-up was performed by washing the synthesized ionic liquid with ether (3× 50 mL).

Reference： [1]Chinese Chemical Letters,2014,vol. 25,p. 1643 - 1647
[2]Organic Process Research and Development,2009,vol. 13,p. 64 - 66
[3]Green Chemistry,2011,vol. 13,p. 1843 - 1851

72
[ 503148-43-4 ]
[ 80-40-0 ]
[ 503148-46-7 ]

Yield	Reaction Conditions	Operation in experiment
		(1) The product (4.86 g) of Example 50(3) was dissolved in dichloromethane and boron tribromide (7.39 mL) was added at -78C. The mixture was stirred at room temperature for 3 hr. The reaction solution was poured into water and sodium hydrogen carbonate was added to adjust its pH to 8. The mixture was extracted with chloroform. The extract solution was washed with saturated brine, dried and concentrated under reduced pressure to give 1-(2-trifluoromethyl-8-hydroxy-4-quinolyl)piperazine (1.52 g) as a pale-yellow solid.(2) In the same manner as in Example 29(1) and using the above-mentioned compound (0.648 g) and the title compound (0.595 g) of Reference Example 3, 3-{(2S,4S)-1-tert-butoxycarbonyl-4-[4-(2-trifluoromethyl-8-hydroxy-4-quinolyl)-1-piperazinyl]-2-pyrrolizinylcarbonyl}-1,3-thiazolidine (1.30 g) was obtained as a fine yellow solid.(3) Sodium hydride (40 mg) was suspended in DMF (1 mL) and the above-mentioned compound (291 mg) was added under ice-cooling. The mixture was stirred for 10 min. Ethyl p-toluenesulfonate (200 mg) was added to the reaction mixture and the mixture was stirred at 70C for 4 hr. Water was added to the reaction mixture, and the mixture was extracted with chloroform. The extract solution was washed with saturated brine, dried and concentrated under reduced pressure. The residue was purified by silica gel column chromatography to give 3-{(2S,4S)-1-tert-butoxycarbonyl-4-[4-(8-ethoxy-2-trifluoromethyl-4-quinolyl)-1-piperazinyl]-2-pyrrolizinylcarbonyl]-1,3-thiazolidine (280 mg) as a fine yellow solid.(4) In the same manner as in Example 47(5) and using the above-mentioned compound (280 mg), the title compound (141 mg) was obtained as a yellow powder.1H-NMR(DMSO-d6)delta 1.57(3H,t,J=6.9Hz), 2.54(1H,m), 3.02-4.17(16H,m), 4.19-4.46(3H,m), 4.51-5.18(3H,m), 7.42(1H,m), 7.51(1H,s), 7.73-7.77(2H,m), 9.33(1H,brs), 10.94(1H,brs).

Reference： [1]Patent: EP1426366,2004,A1 .Location in patent: Page 41

73
[ 80-40-0 ]
[ 15042-01-0 ]
[ 86404-03-7 ]

Yield	Reaction Conditions	Operation in experiment
65%	With sodium hydrogencarbonate; In N,N-dimethyl-formamide; at 60℃; for 10h;Inert atmosphere;	Formula I (10 g, 0.465 mol) was dissolved in 172 mL of dimethylformamide and then sodium bicarbonate (102 g, 1.605 mol) was added, followed by addition of <strong>[80-40-0]ethyl tosylate</strong> (81 g, 0.404 mol), nitrogen was in purged. The reaction mixture was stirred at 60 C. for 10 hours. After cooled to the room temperature, sodium bicarbonate and salt were filtered and evaporated. After evaporation, 5% sodium bicarbonate (100 mL) was added into crude and extracted for twice with Toluene. The organic phase was washed with water and evaporated. Crystallization from n-heptane gave 55 g formula II (0.225 mol; yield=65%). Intermediate was dissolved in n-propanol (60 mL) and then added 2N HCl (16.9 mL), heat to 60 C., after 2 hours, the solvent was evaporated. re-crystallization from Toluene and n-propanol gave 35 g of formula (III). (0.172 mol; yield 56%)

Reference： [1]Patent: US2010/56809,2010,A1 .Location in patent: Page/Page column 3

74
[ 10342-97-9 ]
[ 107-14-2 ]
[ 80-40-0 ]
[ 950901-91-4 ]

Yield	Reaction Conditions	Operation in experiment
81%		Example 2 Synthesis of (cyanomethyl)diisopropylmethylammonium Tosylate 57.61 g (0.5 mol) of diisopropylmethylamine were initially charged at 50 C. in 500 ml of butyl acetate, and 37.75 g (0.5 mol) of chloroacetonitrile were added. The reaction mixture was stirred at 60 C. for 4 hours. Then 100.13 g (0.5 mol) of ethyl para-toluenesulfonate were added and the reaction mixture was stirred at 80 C. for 60 minutes, in the course of which vigorous evolution of gas was observed. The reaction mixture was cooled slowly to 5 C., and the precipitated solid was washed twice with 50 ml each time of butyl acetate and dried at 60 C. under reduced pressure. 131.42 g (0.41 mol) of (cyanomethyl)diisopropylmethylammonium tosylate were obtained as a colorless solid, corresponding to a yield of 81%. 1H NMR (D2O): delta=7.65 (2H, d); delta=7.32 (2H, d); delta=4.75 (2H, s); delta=4.13 (2H, m); delta=2.97 (3H, s); delta=2.34 (3H, s); delta=1.47 (6H, d); delta=1.42 (6H, d).

Reference： [1]Patent: US2009/149668,2009,A1 .Location in patent: Page/Page column 3

75
meso-(1-pyrenyl)-tris(p-pyridyl)porphyrin [ No CAS ]
[ 80-40-0 ]
5,10,15-tris(N-ethylpyridinium-4-yl)-20-(1-pyrenyl)-21H,23H-porphyrin tosylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
96%	In nitromethane; chloroform; for 120h;Reflux; Inert atmosphere;	Example 18 Synthesis of 5,10,15-tris(N-ethylpyridinium-4-yl)-20-(1-pyrenyl)-21H,23H-porphyrin tosylate ("TEPy3Pyr1P-tos3") To a mixture of 15 ml CH3NO2 and 15 ml CHCl3 (1:1 v/v) 14 mumol TPy3Pyr1P (1), and 1.1 mmol ethyl p-toluene-sulfonate are added. This reaction mixture is refluxed for 120 h under argon atmosphere. The progress of the N-ethylation reaction can be monitored using silica gel TLC and an eluent containing ACN : H2O (sat. KNO3) H2O 8:1:1 (v/v).Then the reaction mixture is evaporated to dryness and dissolved in deionized water and the impurities are extracted with CHCl3. The remaining water fraction is filtered and then evaporated to dryness, which gives the tosylate salt of TEPy3Pyr1P3+. Yield: 96 % 1H-NMR (500 MHz, CD3OD, 303.57 K, delta): 9.46 (d, J = 5.68, 2H, pyridyl-3,5-H-a), 9.32 (d, J = 4.48, 4H, pyridyl-3,5-H-b), 9.13 (s, 4H, beta-pyrrole-H), 8.95 (d, J = 5.68, 2H, pyridyl-2,6-H-a), 8.82 (bs, 2H, beta-pyrrole-H), 8.78 (d, J = 4.48, 4H, pyridyl-2.6-H-b), 8.52 (d, J = 7.50, 1H, pyrenyl-H), 8.48 (bs, 2H, beta-pyrrole-H), 8.20 (d, J = 7.48, 1H, pyrenyl-H), 8.02 (m, 3H, pyrenyl-H), 7.65 (d, J = 7.50, 1H, pyrenyl-H), 7.61 (d, J = 7.89, 6H, tosylate-2,6-H), 7.54 (d, J = 7.06, 1H, pyrenyl-H), 7.28 (d, J = 9.29, 1H, pyrenyl-H), 7.06 (d, J = 9.29, 1H, pyrenyl-H), 6.99 (d, J = 7.89, 6H, tosylate-3,5-H), 5.06 (q, J = 7.28, 2H, N+-CH2-a), 4.95 (q, J = 7.22, 2H, N+-CH2-b), 2.08 (s, 9H, tosylate-CH3), 1.98 (t, J = 7.28, 2H, N+-R-CH3-a), 1.88 (t, J = 7.22, 2H, N+-R-CH3-b), -2.74 (s, 2H, pyrrole-NH) 13C-NMR (125 MHz, CD3OD, 303.57 K, delta): 159.7 (s, 1C, quart. ipso pyrenyl-1-C), 159.5 (s, 3C, quart. ipso pyridyl-1-C), 150.3 (s, 8C, quart. alpha-pyrrole), 144.4 (d, 2C, pyridyl-3,5-CH-a), 144.2 (d, 4C, pyridyl-3,5-CH-b), 143.5 (s, 6C, quart. tosylate-1-C), 141.5 (s, 6C, quart. tosylate-4-C), 136.3 (s, 1C, quart. pyrenyl-C), 134.5 (s, 1C, quart. pyrenyl-C), 134.5. (d, 2C, pyridyl-2,6-CH-a), 134.3 (d, 4H, pyridyl-2,6-CH-b), 133.5 (d, 8C, beta-pyrrole-CH), 133.5 (d, 1C, pyrenyl-CH), 133.1 (s, 1C, quart. pyrenyl-C), 132.7 (s, 3C, quart. tosylate-4-C), 131.4 (s, 1C, quart. pyrenyl-C), 129.7 (d, 6C, tosylate-2,6-CH), 129.4 (d, 1C, pyrenyl-CH), 129.0 (d, 1C, pyrenyl-CH), 128.3 (d, 1C, pyrenyl-CH), 127.3 (d, 1H, pyrenyl-CH), 127.0 (d, 1H, pyrenyl-CH), 126.8 (d, 6C, tosylate-3,5-CH), 126.6 (d, 1C, pyrenyl-CH), 126.3 (d, 1C, pyrenyl-CH), 125.1 (s, 1C, quart. pyrenyl-C), 124.9 (s, 1C, quart. pyrenyl-C), 123.9 (d, 1C, pyrenyl-CH), 122.8 (s, 1C, quart. meso pyrenyl-C), 116.4 (s, 1C, quart. meso pyridyl-C-a), 115.9 (s, 2C, quart. meso pyridyl-C-b), 58.6 (q, 1C, N+-CH2-a), 58.5 (q, 1C, N+-CH2-b), 21.1 (q, 9C, tosylate-CH3), 16.8 (t,1C, N+-R-CH2-a), 16.7 (t, 1C, N+-R-CH2-b) ESI-MS (Methanol, positive ion mode): m/z = 276.20 ([M]3+), 413.87 ([M]2+), 499.67 ([M+tos]2+), 1170.80 ([M+tos2]+) C57H46N73+ theoretical mass = 829.02

Reference： [1]Patent: EP2230242,2010,A1 .Location in patent: Page/Page column 33-34

76
[ 555-16-8 ]
[ 80-40-0 ]
[ 99-77-4 ]

Reference： [1]European Journal of Organic Chemistry,2011,p. 6527 - 6531

77
[ 1397262-94-0 ]
[ 80-40-0 ]
[ 1397262-79-1 ]

Yield	Reaction Conditions	Operation in experiment
62%	With potassium carbonate; In N,N-dimethyl-formamide; for 20h;Inert atmosphere; Reflux;	General procedure: To a suspension of N-(benzofuran-2-ylmethyl)-N'-(hydroxybenzyl)homopiperazine 44 (115 mg, 0.5 mmol, 1 equiv.) and anhydrous K2CO3 (552 mg, 2.0 mmol, 4.0 equiv.) in dry N,N-dimethylformamide (3 mL) RT was added a solution of appropriate 4-methylbenzenesulfonate (1.0 mmol, 2.0 equiv.) in N,N-dimethylformamide (2 mL). The reaction mixture was heated to reflux for 20 h, cooled to RT, treated with water (100 mL), and extracted with Et2O (3 x 60 mL). The combined organic fractions were washed with brine, dried (Na2SO4) and concentrated under reduced pressure to give a crude residue, which was then purified by flash column chromatography on silica gel (95:5 v/v CH2Cl2: MeOH).

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2012,vol. 22,p. 5493 - 5497

78
[ 14002-80-3 ]
[ 80-40-0 ]
[ 25307-88-4 ]

Yield	Reaction Conditions	Operation in experiment
47%	With sodium hydride; In N-methyl-acetamide;	3-1. Preparation of Intermediate Ether Ester Compound 1 mol of sodium hydride was added to the solvent dimethylformamide, and 1 mol of hydroxypivalic acid methyl ester was added thereto while the temperature of the solution did not exceed 30 C. The solution was stirred at room temperature for 90 minutes. Then, 1.2 mol of p-toluenesulfonic acid ethyl ester was added to the solution while the temperature of the solution did not exceed 30 C. Then, a water/hexane mixture having the same mass as that of the dimethylformamide was added to and mixed with the solution, after which water was removed therefrom. The resulting organic material was concentrated, and the residue was fractionated under reduced pressure 76~79 C., thereby obtaining the intermediate 3-methoxy-2,2-dimethylpropionic acid methyl ester at a yield of 47%.

Reference： [1]Patent: US2012/251724,2012,A1

79
[ 14002-80-3 ]
[ 80-40-0 ]
[ 58687-24-4 ]

Yield	Reaction Conditions	Operation in experiment
34%	With sodium hydride; In N-methyl-acetamide;	2-1. Preparation of Intermediate Ether Ester Compound 1 mol of sodium hydride was added to the solvent dimethylformamide, and 1 mol of hydroxypivalic acid methyl ester was added thereto while the temperature of the solution did not exceed 30 C. The solution was stirred at room temperature for 90 minutes. Then, 1.2 mol of p-toluenesulfonic acid ethyl ester was added to the solution while the temperature of the solution did not exceed 30 C. Then, a water/hexane mixture having the same mass as that of the dimethylformamide was added to and mixed with the solution, after which water was removed therefrom. The resulting organic material was concentrated, and the residue was fractionated at atmospheric pressure and 108~111 C., thereby obtaining the intermediate 3-ethoxy-2,2-dimethylpropionic acid methyl ester at a yield of 34%.
34%		1 mol of sodium hydride was added to the solvent dimethylformamide, and 1 mol of hydroxypivalic acid methyl ester was added thereto while the temperature of the solution did not exceed 30 C. The solution was stirred at room temperature for 90 minutes. Then, 1.2 mol of p-toluenesulfonic acid ethyl ester was added to the solution while the temperature of the solution did not exceed 30 C. Then, a water/hexane mixture having the same mass as that of the dimethylformamide was added to and mixed with the solution, after which water was removed therefrom. The resulting organic material was concentrated, and the residue was fractionated at atmospheric pressure and 108?111 C., thereby obtaining the intermediate 3-ethoxy-2,2-dimethylpropionic acid methyl ester at a yield of 34%.

Reference： [1]Patent: US2012/251724,2012,A1
[2]Patent: US2014/309456,2014,A1 .Location in patent: Paragraph 0074

80
[ 2799-07-7 ]
[ 80-40-0 ]
[ 64949-90-2 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2013,vol. 23,p. 1394 - 1397

81
[ 26687-82-1 ]
[ 80-40-0 ]
[ 33464-81-2 ]

Yield	Reaction Conditions	Operation in experiment
93%	With potassium carbonate; In acetone; at 20℃; for 3h;	General procedure: To a stirred solution of <strong>[26687-82-1]arctigenin</strong> 1 (180 mg,0.4 mmol) in 3 mL acetone were added K2CO3 (110 mg, 0.8 mmol)and R0X (0.6 mmol) at room temperature. Then the mixture wasstirred at room temperature for 3 h. After completion of the reaction,water (20 mL) was added, and the solution was extractedwith EtOAc (3 20 mL). The combined organic extracts werewashed with brine, dried, filtered, and concentrated under reducedpressure. The crude product was purified by chromatography onsilica gel from (EtOAc/PE = 1/6) to afford the pure product 4a-d.

Reference： [1]Bioorganic and Medicinal Chemistry,2013,vol. 21,p. 3882 - 3893

82
[ 1436123-78-2 ]
[ 80-40-0 ]
[ 1609534-94-2 ]

Yield	Reaction Conditions	Operation in experiment
63%	In acetone; at 20℃; for 29h;Reflux;	Example 8: 1 , 1 -Diethyl-4-(2-pyridyl)-homopiperazinium Tosylate (ASM-037) To a solution of 1-ethyl-4-(2-pyridyl)homopiperazine (1.99 g, 9.7 mmol) in acetone (15 mL) was added ethyl p-toluenesulfonate (3.9 g, 19.4 mmol). The mixture was first stirred at room temperature. After 18 h, the reaction was not complete, then the mixture was heated gently to reflux temperature for 7 h. There was some starting material left, ethyl p-toluenesulfonate (3.9 g, 19.4 mmol) was added and the reaction was stirred for 4 additional days. The mixture was cooled to room temperature and filtered. The white solid was dried at room temperature under vacuum to afford 2.46 g (63% yield) of ASM-037: LC-UV-MS analysis: 100% homogeneity (RT = 13.70 min) using UV detection at 240 nm and CN column with ACN-H20 (0.1 % formic acid) as gradient eluent; ES(+) m/z 234.2 (M - TsO"); ES(-) m/z 171 (TsO"); H N MR D20 (ppm): 8.03 (d, 1 H), 7.63 (d, 3H), 7.29 (d, 2H), 6.73 (m, 2H), 3.87 (br s, 2H), 3.60 (t, 2H), 3.50 (m, 2H), 3.32 (m, 6H), 2.32 (s, 3H), 2.20 (br s, 2H), 1.26 (t, 6H).
63%	In acetone; at 20℃; for 121h;Reflux; Inert atmosphere;	To a solution of 1-ethyl-4-(2-pyridyl)homopiperazine (1.99 g, 9.7 mmol) in acetone (15 mL) was added ethyl p-toluenesulfonate (3.9 g, 19.4 mmol). The mixture was first stirred at room temperature. After 18 h, the reaction was not complete, then the mixture was heated gently to reflux temperature for 7 h. There was some starting material left, ethyl p-toluenesulfonate (3.9 g, 19.4 mmol) was added and the reaction was stirred for 4 additional days. The mixture was cooled to room temperature and filtered. The white solid was dried at room temperature under vacuum to afford 2.46 g (63% yield) of the title compound: LC-UV-MS analysis: 100% homogeneity (RT = 13.70 min) using UV detection at 240 nm and CN column with ACN-H20 (0.1 % formic acid) as gradient eluent; ES(+) m/z 234.2 (M - TsO ); ES(-) m/z 171 (TsO ); H NMR D20 (ppm): 8.03 (d, 1 H), 7.63 (d, 3H), 7.29 (d, 2H), 6.73 (m, 2H), 3.87 (br s, 2H), 3.60 (t, 2H), 3.50 (m, 2H), 3.32 (m, 6H), 2.32 (s, 3H), 2.20 (br s, 2H), 1.26 (t, 6H).

Reference： [1]Patent: WO2014/71512,2014,A1 .Location in patent: Page/Page column 18; 19
[2]Patent: WO2015/149178,2015,A1 .Location in patent: Page/Page column 16

83
[ 1609535-00-3 ]
[ 80-40-0 ]
[ 1609535-02-5 ]

Yield	Reaction Conditions	Operation in experiment
93%	In acetone; for 41h;Reflux;	Step 4: To a solution of 1 -(phenyl-4-benzyloxy)-4-ethyl-homopiperazine (4.51 g, 14.55 mmol) in acetone (20 mL) was added EtOTs (8.73 g, 43.65 mmol). The mixture was stirred at reflux for 41 h, and after cooling down, MTBE (30 mL) was added. After stirring 15 min, the precipitate was filtered and washed with MTBE, dried under vacuum to afford product 1 , 1 -Diethyl-4- (phenyl-4-benzyloxy)-homopiperazinium tosylate (6.88 g, 93%) as a beige solid: H NMR (400 MHz, CD3OD) delta 7.72 (d, 2H), 7.36 (m, 5H), 7.24 (d, 2H), 6.93 (m, 2H), 6.82 (m, 2H), 5.03 (s, 2H), 3.67 (br s, 2H), 3.61 (m, 2H), 3.46 (m, 8H), 2.38 (s, 3H), 2.23 (br s, 2H), 1.33 (t, 6H); (M)+ : 339.3.
93%	In acetone; for 41h;Inert atmosphere; Reflux;	To a solution of 1 -(phenyl-4-benzyloxy)-4-ethyl-homopiperazine (4.51 g, 14.55 mmol) in acetone (20 mL) was added EtOTs (8.73 g, 43.65 mmol). The mixture was stirred at reflux for 41 h, and after cooling down, MTBE (30 mL) was added. After stirring 15 min, the precipitate was filtered and washed with MTBE, dried under vacuum to afford product 1 , 1 -Diethyl-4-(phenyl-4-benzyloxy)-homopiperazinium tosylate (6.88 g, 93%) as a beige solid: H NMR (400 MHz, CD3OD) delta 7.72 (d, 2H), 7.36 (m, 5H), 7.24 (d, 2H), 6.93 (m, 2H), 6.82 (m, 2H), 5.03 (s, 2H), 3.67 (br s, 2H), 3.61 (m, 2H), 3.46 (m, 8H), 2.38 (s, 3H), 2.23 (br s, 2H), 1 .33 (t, 6H); (M)+ : 339.3.

Reference： [1]Patent: WO2014/71512,2014,A1 .Location in patent: Page/Page column 20
[2]Patent: WO2015/149178,2015,A1 .Location in patent: Page/Page column 20

84
[ 1609534-98-6 ]
[ 80-40-0 ]
[ 1609534-90-8 ]

Yield	Reaction Conditions	Operation in experiment
90%	In acetone; for 94h;Reflux;	A 5 L three-necked flask, equipped with a mechanical stirrer and a condenser, is charged with 189.55 g (0.93 mol) of 1-phenyl-4-ethyl-homopiperazine and then 1 L of acetone. Ethyl p- toluenesulfonate (371.6 g, 1.86 mol, 2 equiv) plus 200 mL of acetone for wash then added and the mixture was heated gently to reflux temperature. After 4 h, crystals had started to form and 350 ml of acetone were added to facilitate the stirring. After 24 h, HPLC analysis indicated that there was some starting material left. Consequently, 1 additional equivalent of TsOEt was added (186 g) and the mixture was further heated to reflux. After a total of 94 h, HPLC analysis indicated that the reaction had not progress much further and therefore, the heating was stopped and after 1 h, tert-butyl methyl ether (1 L) was added. The mixture was stirred 15 min, then the crystals were filtered and washed with 5 portions of 500 mL of f-butyl methyl ether. The fine white needles were dried at room temperature under vacuum for 24 hours to afford 336.86 g (90% yield) of ASM-024: mp 167.5-168.8C; LC-UV-MS analysis: 100% homogeneity (RT = 13.4 min) using UV detection at 240 nm and CN column with ACN- H2O (0.1 % formic acid) as gradient eluent; ES(+) m/z 233.2 (MTsO-); ES(-) m/z 171 (TsO-). 1H NMR (D2O) delta 7.74 (d, 2H), 7.40 (m, 4H), 6.93 (m, 3H), 3.75 (br s, 2H), 3.54 (m, 4H), 3.37 (m, 6H), 2.42 (s, 3H), 2.23 (br s, 2H), 1.32 (t, 6H); 13C NMR (D2O) delta 6.7, 20.3, 21.5, 42.6, 46.2, 54.5, 59.5, 60.3, 1 12.8, 1 17.6, 125.2, 129.0, 129.4, 140.4, 141.2, 147.9. The crude product ASM-024 (222.1 1 g) was dissolved in hot CH2Cl2 (750 mL). Then, tBuOMe (160 mL) was added slowly in order to create a mild milky vein and until the appearance of the first crystal, and the mixture was left at room temperature for 3 h. Then, the white solid was filtered, washed with tBuOMe (500 mL) and dried under vacuum. For the second and third recrystallization, the same procedure was used with CH2Cl2 (750 mL)/ fBuOMe (1 10 mL) and CH2Cl2 (720 mL)/ tBuOMe (120 mL) respectively, to afford 21 1.8 g of ASM-024 (99% recovery): LCMS analysis for EtOTs indicated 0.99 ppm.
90%	In acetone; for 94h;Inert atmosphere; Reflux;	A 5 L three-necked flask, equipped with a mechanical stirrer and a condenser, is charged with 189.55 g (0.93 mol) of 1-phenyl-4-ethyl-homopiperazine and then 1 L of acetone. Ethyl p-toluenesulfonate (371.6 g, 1.86 mol, 2 equiv) plus 200 mL of acetone for wash then added and the mixture was heated gently to reflux temperature. After 4 h, crystals had started to form and 350 ml of acetone were added to facilitate the stirring. After 24 h, HPLC analysis indicated that there was some starting material left. Consequently, 1 additional equivalent of TsOEt was added (186 g) and the mixture was further heated to reflux. After a total of 94 h, HPLC analysis indicated that the reaction had not progress much further and therefore, the heating was stopped and after 1 h, t- butyl methyl ether (1 L) was added. The mixture was stirred 15 min, then the crystals were filtered and washed with 5 portions of 500 mL of f-butyl methyl ether. The fine white needles were dried at room temperature under vacuum for 24 hours to afford 336.86 g (90% yield) of the title compound: mp 167.5-168.8C; LC-UV-MS analysis: 100% homogeneity (RT = 13.4 min) using UV detection at 240 nm and CN column with ACN- H20 (0.1 % formic acid) as gradient eluent; ES(+) m/z 233.2 (M - TsO ); ES(-) m/z 171 (TsO ). H NMR (D20) delta 7.74 (d, 2H), 7.40 (m, 4H), 6.93 (m, 3H), 3.75 (br s, 2H), 3.54 (m, 4H), 3.37 (m, 6H), 2.42 (s, 3H), 2.23 (br s, 2H), 1.32 (t, 6H); 3C NMR (D20) delta 6.7, 20.3, 21.5, 42.6, 46.2, 54.5, 59.5, 60.3, 1 12.8, 1 17.6, 125.2, 129.0, 129.4, 140.4, 141.2, 147.9. The crude product ASM-024 (222.1 1 g) was dissolved in hot CH2CI2 (750 mL). Then, fBuOMe (160 mL) was added slowly in order to create a mild milky vein and until the appearance of the first crystal, and the mixture was left at room temperature for 3 h. Then, the white solid was filtered, washed with fBuOMe (500 mL) and dried under vacuum. For the second and third recrystallization, the same procedure was used with CH2CI2 (750 mL)/ fBuOMe (1 10 mL) and CH2CI2 (720 mL)/ fBuOMe (120 mL) respectively, to afford 211.7 g of ASM-024 (99% recovery).
211.7 g	In acetone; for 94h;Reflux;	Example 5: 1 , 1 -Diethyl-4-phenyl-homopiperazinium Tosylate (ASM-024) A 5 L three-necked flask, equipped with a mechanical stirrer and a condenser, is charged with 189.55 g (0.93 mol) of 1 -phenyl-4-ethyl-homopiperazine and then 1 L of acetone. Ethyl p- toluenesulfonate (371.6 g, 1.86 mol, 2 equiv) plus 200 mL of acetone for wash then added and the mixture was heated gently to reflux temperature. After 4 h, crystals had started to form and 350 ml of acetone were added to facilitate the stirring. After 24 h, HPLC analysis indicated that there was some starting material left. Consequently, 1 additional equivalent of TsOEt was added (186 g) and the mixture was further heated to reflux. After a total of 94 h, HPLC analysis indicated that the reaction had not progress much further and therefore, the heating was stopped and after 1 h, f-butyl methyl ether (1 L) was added. The mixture was stirred 15 min, then the crystals were filtered and washed with 5 portions of 500 mL of f-butyl methyl ether. The fine white needles were dried at room temperature under vacuum for 24 hours to afford 336.86 g (90% yield) of ASM-024: mp 167.5-168.8C; LC-UV-MS analysis: 100% homogeneity (RT = 13.4 min) using UV detection at 240 nm and CN column with ACN- H20 (0.1 % formic acid) as gradient eluent; ES(+) m/z 233.2 (M - TsO"); ES(-) m/z 171 (TsO"). H NMR (D20) delta 7.74 (d, 2H), 7.40 (m, 4H), 6.93 (m, 3H), 3.75 (br s, 2H), 3.54 (m, 4H), 3.37 (m, 6H), 2.42 (s, 3H), 2.23 (br s, 2H), 1.32 (t, 6H); 3C NMR (D20) delta 6.7, 20.3, 21.5, 42.6, 46.2, 54.5, 59.5, 60.3, 1 12.8, 117.6, 125.2, 129.0, 129.4, 140.4, 141.2, 147.9. The crude product ASM-024 (222.1 1 g) was dissolved in hot CH2CI2 (750 mL). Then, fBuOMe (160 mL) was added slowly in order to create a mild milky vein and until the appearance of the first crystal, and the mixture was left at room temperature for 3 h. Then, the white solid was filtered, washed with fBuOMe (500 mL) and dried under vacuum. For the second and third recrystallization, the same procedure was used with CH2CI2 (750 mL)/ fBuOMe (1 10 mL) and CH2CI2 (720 mL)/ fBuOMe (120 mL) respectively, to afford 21 1.7 g of ASM-024 (99% recovery).

Reference： [1]Patent: WO2014/138975,2014,A1 .Location in patent: Page/Page column 16; 17
[2]Patent: WO2015/149178,2015,A1 .Location in patent: Page/Page column 15
[3]Patent: WO2014/71512,2014,A1 .Location in patent: Page/Page column 17; 18

85
[ 1383630-25-8 ]
[ 80-40-0 ]
[ 1448151-54-9 ]

Yield	Reaction Conditions	Operation in experiment
79.1%	In toluene; for 6h;Reflux;	6.2. Synthesis of N-Ethyl-N-methyl-3-[(3-methyl-4-nitrophenyl)amino]-N-{3-[(3-methyl-4-nitrophenyl)amino]propyl}-1-propanaminium p-toluene sulfonate N1-Methyl-N3-(3-methyl-4-nitrophenyl)-N1-{3-[(3-methyl-4-nitrophenyl)-amino]propyl}-1,3-propanediamine (52.0 g, 0.13 mol) from step 6.1 was heated under reflux with ethyl p-toluene sulfonate (28.0 g, 0.14 mol) in 500 ml toluene for 6 hours. As the reaction progressed the product separated out in the form of an oily substance. This oil was separated from the supernatant liquid by decanting and dried. On further cooling the oil initially solidified to a glassy material and after drying could be crushed to afford the product as a brown powder. Yield: 60.9 g (79.1%); 1H-NMR (400 MHz, DMSO-d6): delta [ppm]=1.21 (t, 3H); 1.97 (m, 4H); 2.29 (s, 3H); 2.99 (s, 3H); 3.23 (m, 4H); 3.33 (m, 4H); 3.43 (q, 2H); 6.50 (dd, 2H); 6.55 (dd, 2H); 7.18 (d, 2H); 7.20 (br. 2*NH); 7.54 (d, 2H); 7.96 (d, 2H).

Reference： [1]Patent: US2014/245541,2014,A1 .Location in patent: Paragraph 0237

86
[ 1383630-17-8 ]
[ 80-40-0 ]
[ 1383629-63-7 ]

Yield	Reaction Conditions	Operation in experiment
70.8%	In toluene; for 6h;Reflux;	2.2. Synthesis of N-ethyl-N-methyl-3-[(4-nitrophenyl)amino]-N-{3-[(4-nitrophenyl)amino]-propyl}-1-propanaminium p-toluene sulfonate [0227] N1-methyl-N3-(4-nitrophenyl)-N1-{3-[(4-nitrophenyl)amino]propyl}-1,3-propanediamine (40.0 g, 0.10 mol) from step 2.1. was heated under reflux with ethyl p-toluene sulfonate (20.5 g, 0.11 mol) in 500 ml toluene for 6 hours. As the reaction progressed the product separated out in the form of an oily substance. This oil was decanted off from the supernatant liquid and stirred with 500 ml toluene. The oil was removed mechanically from the flask, dried and crushed. Yield: 43.0 g (70.8%); 1H-NMR (400 MHz, DMSO-d6): delta [ppm]=1.19 (t, 3H); 1.96 (m, 4H); 2.29 (s, 3H); 2.98 (s, 3H); 3.27 (m, 4H); 3.33 (m, 6H); 6.68 (d, 4H); 7.17 (d, 2H); 7.39 (br., 2×NH); 7.56 (d, 2H); 8.01 (d, 4H).

Reference： [1]Patent: US2014/245541,2014,A1 .Location in patent: Paragraph 0227

87
[ 80-40-0 ]
ethyl 4-(bromomethyl)benzenesulfonate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
35%	With N-Bromosuccinimide; dibenzoyl peroxide; In benzene;Reflux;	Prepared by modification of a literature procedure [3]. <strong>[80-40-0]Ethyl tosylate</strong> (1.00 g, 5.00 mmol) was refluxed with NBS (1.07 g, 6.00 mmol) and benzoyl peroxide (484 mg, 2.00 mmol) in anhydrous benzene (50 mL) overnight. The reaction mixture was then washed with brine solution and dried with anhydrous magnesium sulfate. The solvent was removed under reduced pressure and the product was isolated using column chromatography (5-30 % ethyl acetate in hexane) to yield 0.488 g (35 %) of a yellow oil.
35%	With N-Bromosuccinimide; dibenzoyl peroxide; In benzene;Reflux;	Prepared by modification of a literature procedure [3]. <strong>[80-40-0]Ethyl tosylate</strong> (1.00 g, 5.00 mmol) was refluxed with NBS (1.07 g, 6.00 mmol) and benzoyl peroxide (484 mg, 2.00 mmol) in anhydrous benzene (50 mL) overnight. The reaction mixture was then washed with brine solution and dried with anhydrous magnesium sulfate. The solvent was removed under reduced pressure and the product was isolated using column chromatography (5-30 % ethyl acetate in hexane) to yield 0.488 g (35 %) of a yellow oil.

Reference： [1]Journal of Organometallic Chemistry,2014,vol. 777,p. 16 - 24
[2]Journal of Organometallic Chemistry,2015,vol. 777,p. 16 - 24

88
[ 103-19-5 ]
[ 80-40-0 ]

Yield	Reaction Conditions	Operation in experiment
13%	With sodium hypochlorite pentahydrate; In ethanol; at 20℃; for 7.7h;	General procedure: To a solution of di-p-tolyldisulfide (739.2 mg, 3.0mmol) in acetic acid (11 mL), NaOCl?5H2O (2.47 g, 15.0mmol) was added and stirred at room temperature for 65min. Saturated aqueous sodium thiosulfate (4 mL) and dichloromethane (15 mL) was added to the reaction mixture. The organic layer was separated and the aqueous phase was extracted with dichloromethane (15mL x 2). The combined extracts were dried over anhydrous sodium sulfate, and evaporated to afford p-toluenesulfonyl chloride (915.0 mg, 80%) as colorless crystals. This product is pure enough without further purifications, and is consistent with the commercial reagent.

Reference： [1]Chemistry Letters,2015,vol. 44,p. 185 - 187

89
(1S,2S,3S,5R,6S)-3'-((allyloxy)carbonyl)-3-fluoro-5'-oxospiro[bicyclo[3.1.0]hexane-2,4'-oxazolidine]-6-carboxylic acid [ No CAS ]
[ 80-40-0 ]
(1S,2S,3S,5R,6S)-3'-allyl 6-ethyl 3-fluoro-5'-oxospiro[bicyclo[3.1.0]hexan-2,4'-oxazolidine]-3',6-dicarboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
68 mg		(1) (1S,2S,3S,5R,6S)-3'-Allyl 6-ethyl 3-fluoro-5'-oxospiro[bicyclo[3.1.0]hexan-2,4'-oxazolidine]-3',6-dicarboxylate (Reference Example 1-1) To a suspension of (1S,2S,3S,5R,6S)-3'-((allyloxy)carbonyl)-3-fluoro-5'-oxospiro[bicyclo[3.1.0]hexan-2,4'-oxazolidine]-6-carboxylic acid obtained below in Example A-1 (A-1-2, 200 mg) in N,N-dimethylformamide (6 mL), cesium carbonate (261 mg) was added, and the mixture was stirred at room temperature for 30 minutes. <strong>[80-40-0]Ethyl tosylate</strong> (201 mg) was added and the mixture was stirred at room temperature for 1 hour. To the reaction mixture, water was added, and the mixture was extracted twice with ethyl acetate. The combined organic layer was washed once with water and once with brine, sequentially, and then the ethyl acetate layer was dried over anhydrous sodium sulfate. The insoluble was filtered off, the filtrate was concentrated under reduced pressure, and the resulting residue was purified by silica gel column chromatography (silica gel cartridge, hexane:ethyl acetate = 100:0 - 50:50) to give (1S,2S,3S,5R,6S)-3'-allyl 6-ethyl 3-fluoro-5'-oxospiro[bicyclo[3.1.0]hexan-2,4'-oxazolidine]-3',6-dicarboxylate (Reference Example 1-1, 68 mg) as a colorless amorphous. 1H NMR (600 MHz, CHLOROFORM-d) delta = 6.01-5.92(m, 1H), 5.60(d, J = 4.5 Hz, 1H), 5.37-5.30(m, 1H), 5.29-5.21(m, 2H), 4.77-4.62(m, 3H), 4.20-4.12(m, 2H), 2.62-2.46(m, 2H), 2.37-2.25(m, 1H), 2.22-2.17(m, 1H), 1.27(t, J = 1.0 Hz, 3H)
68 mg		The obtained (1S, 2S, 3S, 5R, 6S)-3 '- (((allyloxy) carbonyl) -3-fluoro-5'-oxospiro [bicyclo [3.1.0] hexane-2,4'-oxazolidine] - 6-carboxylic acid(Reference Example 3-2, 200 mg)In N, N-dimethylformamide (6 mL)Cesium carbonate (261 mg) was added,And the mixture was stirred at room temperature for 30 minutes.<strong>[80-40-0]Ethyl tosylate</strong> (201 mg) was further added,And the mixture was stirred at room temperature for 1 hour. Water was added to the reaction solution,Extracted twice with ethyl acetate. The combined organic layers were washed once with water,After washing sequentially with saturated saline solution,The ethyl acetate layer was dried over anhydrous sodium sulfate.Insolubles were filtered off, the filtrate was concentrated under reduced pressure,The residue was purified by silica gel column chromatography (silica gel cartridge, hexane: ethyl acetate = 100: 0 to 50:50) to give (1 S, 2S, 3S, 5R, 6S) -3'- allyl 6- -5'-oxospiro [bicyclo [3.1.0] hexane-2,4'-oxazolidine] -3 ', 6-dicarboxylate (Reference Example 3-3, 68 mg) as colorless amorphous.

Reference： [1]Patent: EP2857385,2015,A1 .Location in patent: Paragraph 0042; 0043; 0044
[2]Patent: JP2015/127325,2015,A .Location in patent: Paragraph 0109; 0114; 0115

90
[ 98639-91-9 ]
[ 80-40-0 ]
2-(methylsulfinyl)-N-ethyl-benzimidazole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
86%		Galvanostatic electrolysis was performed in a two-compartment cell [15] equipped with platinum spirals as cathode (apparent area ?1 cm2) and anode (apparent area ?0.5 cm2) using applied constant current I = 25 mA and total charge Q = 1.1 electrons per molecule 1. The catholyte starting material was 1 (18 mg, 0.1 mmol), CH3CN (0.3 ml), Et4NBF4 (21 mg, 0.1 mmol), and the anolyte was1-butyl-3-methylimidazolium tetrafluoroborate (0.3 ml). At the end of the electrolysis, MeI (0.11 mmol, 7 muL) was added to the cathode compartment and the reaction was prolonged at rt under magnetic stirring for 2 h. The mixture was then concentrated in vacuum and directly purified by flash chromatography (eluent mixture: hexane/AcEt) to obtain pure product 3a in 76% yield as an amorphous solid.

Reference： [1]Synthetic Communications,2015,vol. 45,p. 1783 - 1791

91
N-(6-[(3R,4S)-3-fluoropiperidin-4-yl]oxy}pyridin-3-yl)-3-methyl-5-[5-(trifluoromethyl)pyrazin-2-yl]amino}-1,2-thiazole-4-carboxamide trifluoroacetate [ No CAS ]
[ 80-40-0 ]
N-(6-[(3R,4S)-1-ethyl-3-fluoropiperidin-4-yl]oxy}pyridin-3-yl)-3-methyl-5-[5-(trifluoromethyl)pyrazin-2-yl]amino}-1,2-thiazole-4-carboxamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
46 mg	With potassium carbonate; potassium iodide; In acetonitrile; at 70℃; for 6h;Inert atmosphere;	A mixture of the crude salt of N-(6-f[(3R,4S)-3-fluoropiperidin-4-yl]oxypyridin-3-yl)-3-methyl-5-f[5-(trifluoromethyl)pyrazin-2-yl]amino-1 , 2-thiazole-4-carboxamidewith trifluoroacetic acid [Example 143] (126 mg, 0.25 mmol, 1.0 eq), ethyl 4- methylbenzenesulfonate (CAS-RN: 80-40-0) (51 mg, 0.25 mmol, 1 eq), potassium carbonate (175 mg, 1.26 mmol, 5.0 eq) and potassium iodide (4mg, 0.03 mmol, 0.1 eq) was taken up in 6 mL acetonitrile. Afterwards the reaction mixture was stirredat an environmental temperature of 70C for 6 h under an atmosphere of argon. On cooling, the reaction mixture was diluted in dichloromethane and ethanol (9/1) and filtered. All volatile components were removed in vacuo and the final purification was conducted via preparative HPLC (Method B) to give 46 mg (33 % yield of theory) of the title compound.UPLC-MS (Method 2): R = 0.85 mm; MS (EI0): m/z = 526 [M+H].1H-NMR (400MHz, THF) delta [ppm]: 0.000 (7.24), 1.042 (2.32), 1.059 (4.87), 1.077(2.49), 1.726 (15.81), 2.405 (0.63), 2.423 (1.83), 2.441 (1.81), 2.455 (1.23), 2.459(0.72), 2.664 (10.03), 3.577 (14.31), 3.580 (16.00), 3.582 (14.43), 6.763 (1.30),6.785 (1.35), 8.086 (0.83), 8.093 (0.88), 8.109 (0.85), 8.115 (0.87), 8.450 (1.32),8.456 (1.31), 8.557 (1.23), 8.561 (1.31), 8.638 (1.36).

Reference： [1]Patent: WO2015/113920,2015,A1 .Location in patent: Page/Page column 438; 439

92
5-[(4-cyanopyridin-2-yl)amino]-3-methyl-N-[6-(piperidin-4-yloxy)pyridin-3-yl]-1,2-thiazole-4-carboxamide trifluoroacetate [ No CAS ]
[ 80-40-0 ]
5-[(4-cyanopyridin-2-yl)amino]-N-{6-[(1-ethylpiperidin-4-yl)oxy]pyridin-3-yl}-3-methyl-1,2-thiazole-4-carboxamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
25 mg	With potassium carbonate; potassium iodide; In acetonitrile; at 70℃;Inert atmosphere; Sealed tube;	A mixture of the trifluoro acetate salt of 5-[(4-cyanopyridin-2-yl)amino]-3-methyl-N-[6-(piperidin-4-yloxy)pyridin-3-yl]- 1, 2-thiazole-4-carboxamide [Example 24] (200mg, 70% purity, 0.32 mmol, 1 .0 eq), ethyl 4-methylbenzenesulfonate (CAS-RN: 80-40-0) (97 mg, 0.48 mmol, 1.5 eq), potassium carbonate (222 mg, 1.6 mmol, 5.0 eq)and potassium iodide (5 mg, 0.32 mmol, 0.1 eq) in 7.5 mL acetonitrile was placedin a microwave vial that was flushed with argon. Afterwards, the vial was sealedand the reaction mixture was stirred at an environmental temperature of 70 C overnight. The volatile components were removed in vacuo and the final purification was conducted via preparative HPLC (Method A) to give 25 mg (17 % yield of theory) of the title compound.UPLC-MS (Method 2): R = 0.84 mm; MS (EI0): m/z = 464 [M+H].1H NMR (400 MHz, DMSO-d6): oe [ppm] = 1.04 (t, 3 H), 1.60 - 1.80 (m, 2 H), 1.96 -2.11 (m, 2 H), 2.24 - 2.42 (m, 2 H), 2.80 - 2.96 (m, 2 H), 4.97 (tt, 1 H), 6.75 (d, 1H), 6.81 (d, 1 H), 7.53 (5 br, 1 H), 8.10 - 8.28 (m, 1 H), 8.40 (d, 1 H), 8.54 (d, 1 H),13.53 (5 br, 1 H), ix CH2 and 1xCH3 obscured by the solvent signal, 1xNH notdetected.

Reference： [1]Patent: WO2015/113920,2015,A1 .Location in patent: Page/Page column 231

93
1-methyl-4-phenylhomopiperazine [ No CAS ]
[ 80-40-0 ]
1-ethyl-1-methyl-4-(phenyl)-homopiperazinium tosylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
85%	In acetone; for 22h;Inert atmosphere; Reflux;	To a solution of 1-methyl-4-(phenyl)-homopiperazine (2.13 g, 1 1.21 mmol) in acetone (14 mL) was added ethyl p-toluenesulfonate (4.5 g, 22.42 mmol). The mixture was heated gently to reflux temperature for 22 h. The mixture was cooled to room temperature, then f-butyl methyl ether (10 mL) was added. The mixture was stirred 15 min, then filtered and washed with 2 portions of 10 mL of f-butyl methyl ether. The white solid was recrystallized twice in dichloromethane/ f-butyl methyl ether (40 mL/5 mL), then dried at room temperature under vacuum to afford 3.73 g (85% yield) of the title compound: LC-UV-MS analysis: 100% homogeneity (RT = 8.20 min) using UV detection at 240 nm and CN column with ACN-H20 (0.1 % formic acid) as gradient eluent; mp = 167.5-168.7 C; ES(+) m/z 219.2 (M - TsO ); ES(-) m/z 171 (TsO ); H NMR D20 (ppm): 7.64 (d, 2H), 7.29 (m, 4H), 6.83 (m, 3H), 3.64 (br s, 2H), 3.29 (m, 8H), 2.94 (s, 3H), 2.32 (s, 3H), 2.13 (br s, 2H), 1.27 (t, 3H); 3C NMR D20 (ppm): 6.9, 20.0, 21.6, 42.8, 46.2, 48.0, 59.7, 61.9, 62.3, 1 12.8, 1 17.9, 124.9, 129.0, 129.4, 139.2, 141.9, 147.7.

Reference： [1]Patent: WO2015/149178,2015,A1 .Location in patent: Page/Page column 16; 17

94
1-ethyl-4-(4-fluorophenyl)homopiperazine [ No CAS ]
[ 80-40-0 ]
1,1-diethyl-4-(4-fluorophenyl)-homopiperazinium tosylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
81%	In acetone; for 24h;Reflux; Inert atmosphere;	To a solution of 1-ethyl-4-(4-fluorophenyl)homopiperazine (2.27 g, 10.24 mmol) in acetone (12 mL) was added ethyl p-toluenesulfonate (4.1 g, 20.5 mmol). The mixture was heated gently to reflux temperature for 24 h. The mixture was cooled to room temperature, then f-butyl methyl ether (10 mL) was added. The mixture was stirred 15 min, then filtered and washed with 2 portions of 10 mL of f-butyl methyl ether. The white solid was dried at room temperature under vacuum to afford 3.50 g (81 % yield) of the title compound : LC-UV-MS analysis: 100% homogeneity (RT = 10.43 min) using UV detection at 240 nm and CN column with ACN-H20 (0.1 % formic acid) as gradient eluent; Exact Mass calcd for C15H24N2F (M+) 251.1915, found 251.1918, C7H7S03 (M ) 171.01 17, found 171.0121 ; mp = 169.4-170.5 C; H NMR D20 (ppm): 7.61 (d, 2H), 7.28 (d, 2H), 7.01 (t, 2H), 6.80 (m, 2H), 3.63 (br s, 2H), 3.46 (m, 2H), 3.33 (m, 8H), 2.31 (s, 3H), 2.13 (br s, 2H), 1.22 (t, 6H); 3C NMR D20 (ppm): 7.7, 21.2, 22.6, 44.7, 48.5, 55.7, 60.6, 61.5, 1 15.7, 1 15.8, 1 16.4, 1 16.7, 126.2, 130.1 , 141.0, 142.6, 145.8, 145.9, 155.2, 158.3.

Reference： [1]Patent: WO2015/149178,2015,A1 .Location in patent: Page/Page column 16

95
[ 371-41-5 ]
[ 80-40-0 ]
[ 2924-75-6 ]

Yield	Reaction Conditions	Operation in experiment
71%	With 1,8-diazabicyclo[5.4.0]undec-7-ene; In toluene; at 20℃; for 16h;Inert atmosphere;	To a solution of ethyl 4-methylbenzenesulfonate (400 mg, 2.0 mmol, 1.0 eq.) and 4-fluorothiophenol (260 mul, 2.4 mmol, 1.2 eq.) in toluene (12 ml) was added DBU (400 mul, 2.6 mmol, 1.3 eq.). After stirring for 16 h at rt under an atmosphere of argon, the mixture was diluted with CH2Cl2 (15 ml) and washed with aq. sat. NH4Cl (10 ml) and brine. The separated organic layer was dried over Na2SO4 and concentrated under reduced pressure. Column chromatography on silica gel (CyH) afforded the desired product as slightly yellow oil (222 mg, 71%).

Reference： [1]Journal of Fluorine Chemistry,2016,vol. 182,p. 121 - 126

96
[ 80-40-0 ]
[ 1193-02-8 ]
[ 3463-02-3 ]

Yield	Reaction Conditions	Operation in experiment
52%	With 1,8-diazabicyclo[5.4.0]undec-7-ene; In toluene; at 20℃; for 15h;Inert atmosphere;	To a solution of ethyl 4-methylbenzenesulfonate (220 mg, 1.1 mmol, 1.1 eq.) and 4-aminothiophenol (125 mg, 1.0 mmol, 1.0 eq.) in toluene (6 ml) was added DBU (180 mul, 1.2 mmol, 1.2 eq.). After stirring for 15 h at rt under an atmosphere of argon, the mixture was diluted with CH2Cl2 (10 ml) and washed with aq. sat. NH4Cl (10 ml), brine, dried over Na2SO4 and concentrated under reduced pressure to give a yellow-green oil. Column chromatography on silica gel (CyH/EtOAc 10:1 8:1) afforded the desired product as yellow oil (88 mg, 52%).

Reference： [1]Journal of Fluorine Chemistry,2016,vol. 182,p. 121 - 126

97
[ 1074-36-8 ]
[ 80-40-0 ]
[ 13205-49-7 ]

Yield	Reaction Conditions	Operation in experiment
43%	With 1,8-diazabicyclo[5.4.0]undec-7-ene; In toluene; at 20℃; for 20h;Inert atmosphere;	To a solution of ethyl 4-methylbenzenesulfonate (300 mg, 1.5 mmol, 1.0 eq.) in toluene (9 ml) were added 4-mercaptobenzoic acid (278 mg, 1.8 mmol, 1.2 eq.) and DBU (300 mul, 2.0 mmol, 1.3 eq.) and the mixture was stirred for 20 h at rt. The reaction was quenched with aq. sat NH4Cl (3 ml) and was diluted with H2O and CH2Cl2. The aqueous layer was extracted with CH2Cl2 (3 x 20 ml) and the combined organic layers were washed with brine, dried over Na2SO4 and concentrated under reduced pressure. Separation via column chromatography on silica gel (CyH/EtOAc 1:1) afforded the desired product as white solid (118 mg, 43%).

Reference： [1]Journal of Fluorine Chemistry,2016,vol. 182,p. 121 - 126

98
[ 80-40-0 ]
[ 2682-45-3 ]
C₄₀H₄₀ClN₂S₂⁽¹⁺⁾ [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2016,vol. 138,p. 10112 - 10115

99
[ 59729-19-0 ]
[ 80-40-0 ]
chloride [ No CAS ]
C₄₈H₄₄N₈Zn⁽⁴⁺⁾*4Cl^(1-) [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		The porphyrin ZnTE-2-PyPCl4 was synthesized by alkylation of the precursor Zn(II) meso-tetrakis(2-pyridyl)porphyrin (ZnT-2-PyP) [69] using an adaptation of a literature procedure [70]. ZnT-2-PyP(10 mg) and <strong>[80-40-0]ethyl tosylate</strong> (400 muL = 469 mg) were dissolved in N,N-dimethylformamide (DMF, 2 mL)and heated to 110 C under magnetic stirring for 24 h. The ethylation reaction was monitored by thinlayer chromatography and electronic absorption spectroscopy as reported for the Mn analogue [71]. The resulting ZnTE-2-PyP4+ sample was isolated and purified as the chloride salt (ZnTE-2-PyPCl4) as described elsewhere [17,18]. Spectroscopic characterization data for ZnTE-2-PyP4+ (ZnP) were identicalto those previously reported [17]. After synthesis, the CdTe QDs and ZnP solutions were diluted to aconcentration of 10-6 mol·L-1.

Reference： [1]Molecules,2015,vol. 20,p. 8893 - 8912

100
[ 13278-41-6 ]
[ 80-40-0 ]
ethyl 2-(naphthalen-1-ylamino)benzoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
2.2 g	With potassium carbonate; In 1-methyl-pyrrolidin-2-one; at 90℃; for 24h;	TAM 008-B (2.6 g), ethyl para-toluenesulfonate 2.2 g, potassium carbonate 1.6 g and N-methylpyrrolidone 25 mL were placed in a flask and heated and stirred at 90 C. for 24 hours.After cooling, 200 mL of water was added, the mixture was extracted with ethyl acetate, and the collected organic phases were dried with sodium sulfate.This was produced by silica gel column chromatography to obtain 2.2 g of TAM 008-C.
2.2 g	With potassium carbonate; In 1-methyl-pyrrolidin-2-one; at 90℃; for 24h;	TAMOO4-13 (2.6 g), 2.2 g of ethyl p-toluenesulfonate,1.6 g of potassium carbonate, and 25 mE of N-meth90ylpyrrolidone were put into a flask, followed by heating and stirring at 90 C. for 24 hours. After cooling, 200 mEwater was added thereto, followed by extraction with ethyl acetate, and the combined organic phase was dried over sodium sulfate. This was purified by silica gel colunm chromatography to obtain 2.2 g of TAMOO4-A.

Reference： [1]Patent: JP2016/196614,2016,A .Location in patent: Paragraph 0195
[2]Patent: US2016/376234,2016,A1 .Location in patent: Paragraph 0619

101
[ 80-40-0 ]
[ 130930-25-5 ]
(2R,4R)-1-((benzyloxy)carbonyl)-4-ethoxypyrrolidine-2-carboxylic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
23.88%	With sodium hydroxide; In tetrahydrofuran; water; at 55℃;	Step-1 : Preparation of (2R,4R)-l-(benzyloxycarbonyl)-4-ethoxypyrrolidine-2-carboxylic acid (50b) To a solution of (2R,4R)-l-(benzyloxycarbonyl)-4-hydroxypyrrolidine-2-carboxylic acid (15a) (1.14 g, 4.30 mmol) in THF (20 mL) was added a solution of ethyl 4- methylbenzenesulfonate (50a) (1.721 g, 8.60 mmol) in THF (2 mL), followed by NaOH (0.688 g, 17.19 mmol) and water (5 mL). The resulting mixture was heated to 55 C overnight and concentrated in vacuum to dryness. The residue was dissolved in water (10 mL), washed with dichloromethane (3 x 25 mL) and acidified to pH 2 with HCl (1.5 N). The reaction mixture was extracted with dichloromethane (3 x 25 mL) and organic layers were combined, dried over MgS04, filtered and concentrated in vacuum. The residue was purified by flash chromatography (silica gel, eluting with 0-20% MeOH in chloroform) to obtain (2R,4R)-l-(benzyloxycarbonyl)-4-ethoxypyrrolidine-2-carboxylic acid (50b) (301 mg, 1.026 mmol, 23.88 % yield) as a clear oil. MS (ES+) 316.3 (M+Na).

Reference： [1]Patent: WO2017/59178,2017,A1 .Location in patent: Page/Page column 160

102
2-(5,7-diethyl-2-(4-hydroxyphenyl)pyrazolo[1,5-a]pyrimidin-3-yl)-N,N-diethylacetamide [ No CAS ]
[ 80-40-0 ]
[ 1428949-92-1 ]

Yield	Reaction Conditions	Operation in experiment
		6. Synthesis of final product 6:Intermediate 5 (1.52 g, 4 mmol),Was dissolved in 50 mL of anhydrous THF,Cooled to 0 C,NaH (170 mg, 4.4 mmol) was added in portions,After stirring for 20 minutes,Ethyl p-toluenesulfonate (4.44 g, 12 mmol) was added.30 C for 26 hours.Cooled to room temperature,The reaction solution was poured into 200 mL of ice water,Extracted with ethyl acetate (100 mL * 2 times)The organic layer was dried over anhydrous sodium sulfate,Concentrated, column chromatography,To give a yellow oil 6,After immobilization (1.05 g, 45%) was obtained2- (4- (3- (2- (diethylamino) -2-oxoethyl) -5,7-diethylpyrazole [1,5-a] pyrimidin-2-yl) Yl) ethyl-4-methylbenzenesulfonate,Named as the new ligand SXH 1001

Reference： [1]Patent: CN106749279,2017,A .Location in patent: Paragraph 0115; 0117

103
C₂₆H₂₆Cl₂FN₃O₂ [ No CAS ]
[ 80-40-0 ]
C₂₈H₃₀Cl₂FN₃O₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
18%	With triethylamine; In acetonitrile; at 20℃;	Compound T-15 (32 mg, 0.06 mmol) was dissolved in acetonitrile (4 mL), ethyl p-toluenesulfonate (26 mg, 0.13 mmol) and triethylamine (38 mg, 0.38 mmol) were added and the mixture was stirred overnight at room temperature and acetic acid was added. Ethyl acetate (30 mL), water (20 mL), the organic phase was separated, and the residue was purified by high performance liquid chromatography to give compound T-37 (6 mg, 18%).

Reference： [1]Patent: CN103304571,2018,B .Location in patent: Paragraph 0376-0378

104
[ 64-17-5 ]
[ 824-79-3 ]
[ 80-40-0 ]

Yield	Reaction Conditions	Operation in experiment
75%	With [bis(acetoxy)iodo]benzene; at 20℃; for 0.25h;	General procedure: Iodobenzene diacetate (DIB, 0.24 mmol, 1.2 equiv) was added at room temperature to avigorously stirred solution of dichloromethane (0.5 mL), alcohol (0.5 mL), sulfinate (0.2mmol, 1 equiv) and acetic acid (0.01 to 0.05 mL) or TBAC (55.5 mg, 0.2 mmol, 2 equiv) tosolve the sulfonate salt. The mixture was then stirred for 15 min (followed by TLC with amixture of acetic acid/ethyl acetate/hexane) and then filtered on silica with ethyl acetate.The residue was purified by silica gel chromatography with a mixture of ethylacetate/hexane to give sulfonate product 4, 6 and 8.

Reference： [1]Beilstein Journal of Organic Chemistry,2018,vol. 14,p. 1203 - 1207

105
(1R,9S,12S,13R,14S,17R,18E,21S,23S,24R,25S,27R)-12-[(1E)-1-[(1R,3R,4R)-4-hydroxy-3- methoxycyclohexyl]prop-1-en-2-yl]-1-amino-23,25-dimethoxy-14-hydroxy-13,19,21,27-tetramethyl-17-(prop-2-en-1-yl)-11,28-dioxa-4-azatricyclo[22.3.1.0^4,9]octacos-18-ene-2,3,10,16-tetrone [ No CAS ]
[ 80-40-0 ]
(1R,9S,12S,13R,14S,17R,18E,21S,23S,24R,25S,27R)-12-[(1E)-1-[(1R,3R,4R)-4-hydroxy-3-methoxycyclohexyl]prop-1-en-2-yl]-23,25-dimethoxy-1-ethylamino-14-hydroxy-13,19,21,27-tetramethyl-17-(prop-2-en-1-yl)-11,28-dioxa-4-azatricyclo[22.3.1.0(4,9)]octacos-18-ene-2,3,10,16-tetrone [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
5%	With dmap; N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 50℃; for 24h;Inert atmosphere;	To a solution of (13) (25mg, 0.031mmol, leq) in 2mL DMF was added DMAP (1.2mg, O.OlOmmol, 0.3eq) and allowed to stir under N2. Ethyl p-toluenesulfonate (124.2mg, 0.62mmol, 20eq) was added dropwise followed by the addition of DIEA (160.6mg, 1.24mmol, 40eq). The reaction temperature was raised to 50C. After 24 hours, the crude product was purified by HPLC (5% yield). Expected MW: 830.53, Found M+Na+: 853.58.

Reference： [1]Patent: WO2018/112435,2018,A1 .Location in patent: Paragraph 0036; 0473; 0474; 0499; 0500

106
[ 2536-91-6 ]
[ 80-40-0 ]
C₁₀H₁₃N₂S⁽¹⁺⁾ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
65.7%	at 120℃; for 3h;Sealed tube;	1.1 g (6.7 mmol) of 2-amino-6-methylbenzothiazole and 2.0 g (10.0 mmol) of isopropyl 4-ethylbenzenesulfonate were added to a sealed tube and heated at 120 C for 3 h.The obtained crude product was suspended in ethyl acetate.It was then washed twice with diethyl ether.The obtained solid precipitate is further separated and purified by recrystallization from acetone.Finally, 2.037 g of off-white 1-T1 compound is obtained.The yield was 65.7%.

Reference： [1]Patent: CN108424403,2018,A .Location in patent: Paragraph 0113; 0114; 0115; 0116

107
[ 80-40-0 ]
[ 64-17-5 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium hydroxide; In methanol; dichloromethane; at 30℃; for 6h;	General procedure: To a solution of the ester (1 mmol) in CH2Cl2 (9 mL) was added a methanolicsolution of 3 N NaOH (1 mL, 3 mmol), with the final concentration of the alkali being 0.3 N, and the solventmixture CH2Cl2/CH3OH (9:1, v/v, 10 mL). Esters bearing more than one ester moiety needed more equivalentsof NaOH (Table 1). After stirring, the solution became cloudy and the sodium salt of the carboxylic acid beganto precipitate. The progress of the reaction was monitored by thin layer chromatography (TLC). The mixturewas stirred until the ester was consumed (Table 1), the solvents were then removed under vacuum, theresidue was diluted with water (10 mL) and extracted with ethyl acetate or diethyl ether (2x20 mL) to isolatethe water-insoluble alcohol, and/or to remove unreacted ester. The aqueous phase was cooled, acidified to pH~2 with dilute HCl and extracted with AcOEt (2x20 mL). The combined organic layers were dried (Na2SO4) andthe solvent removed to afford the acid. Alternatively, the RCOONa precipitated during the reaction can beisolated by filtration, washed with CH2Cl2 (10 mL), dried and weighed (Yields: 80-96%).

Reference： [1]Arkivoc,2018,vol. 2018,p. 308 - 319

108
3-hydroxy-2-phenylchromeno[4,3-b]pyrrol-4(1H)-one [ No CAS ]
[ 80-40-0 ]
3-ethoxy-2-phenylchromeno[4,3-b]pyrrol-4(1H)-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
85%	With 1,8-diazabicyclo[5.4.0]undec-7-ene; In toluene; for 1.5h;Reflux;	General procedure: A solution of the respective arylglyoxal monohydrate 1(2 mmol) and 4-aminocoumarin 2 (2 mmol) in AcOH(10 ml) was stirred and heated at reflux temperature for 40 min. The reaction mixture was distilled in vacuum toafford crude compound 4, and then an appropriate alkyl p-toluenesulfonate (2 mmol), DBU (0.36 g, 2.4 mmol), andtoluene (8 ml) were added. The reaction mixture was stirred atreflux temperature. After completion of the reaction within1.5 h (monitored by TLC), the solvent was evaporated andthe residue was then extracted with CH2Cl2 (3×10 ml). Thecombined organic extracts were dried over MgSO4,filtered, concentrated, and purified by column chromatography(CH2Cl2) to give the corresponding compound 3. 3-Ethoxy-2-phenylchromeno[4,3-b]pyrrol-4(1H)-one(3a). Yield 445 mg (73%), white solid, mp 228-229 C. 1H NMR spectrum, delta, ppm (J, Hz): 1.31 (3H, t, J = 7.0,CH3); 4.23 (2H, q, J = 7.0, CH2); 7.29-7.41 (3H, m, H Ar);7.44-7.51 (3H, m, H Ar); 7.92 (2H, dd, J = 8.0, J = 1.2, H Ar); 8.28 (1H, dd, J = 7.8, J = 1.5, H Ar); 12.29 (1H, s,NH). 13C NMR spectrum, delta, ppm: 43.8; 98.4; 130.2; 141.7;145.0; 149.9; 151.6; 152.3; 153.8 (2C); 155.2; 156.9 (2C);157.1; 158.6; 160.6; 169.0; 179.5; 184.7. Found, m/z: 328.0937[M+Na]+. C19H15NNaO3. Calculated, m/z: 328.0944.

Reference： [1]Chemistry of Heterocyclic Compounds,2018,vol. 54,p. 1065 - 1069
Khim. Geterotsikl. Soedin.,2018,vol. 54,p. 1065 - 1969,5

109
[ 95-88-5 ]
[ 80-40-0 ]
[ 17715-67-2 ]

Yield	Reaction Conditions	Operation in experiment
89.2%	With sodium hydroxide; In water; at 80℃; for 5h;	In a 300 ml flask, 12.5 g (86.5 mmol) of 4-chlororesorcinol (manufactured by Tokyo Chemical Industry Co., Ltd.),40 g of triethylene glycol monomethyl ether was added and heated to 70 C., and stirring was performed until 4-chlororesorcinol was completely dissolved.After visually confirming that 4-chlororesorcinol was completely dissolved,To this is added 45.1 g (225 mmol) of ethyl p-toluenesulfonate,Thereafter, 48.5 g (242 mmol) of a 20% aqueous solution of sodium hydroxide was slowly added dropwise over 1 hour.Stir for 3 hours after the end of the dropwiseThe temperature was further raised to 80 C., and stirring was performed for 1 hour.Allow to cool to room temperature, add 100 ml of deionized water,Stirring was performed for a while. Let stand in the refrigerator overnight,The precipitate is filtered off,Wash with 200 ml of deionized water and dry at 40 C.15.5 g of yellowish white solid(Yield 89.2%

Reference： [1]Patent: JP2019/99658,2019,A .Location in patent: Paragraph 0074

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Technical Information

• Acyl Group Substitution • Alcohols Convert Acyl Chlorides into Esters • Alcoholysis of Anhydrides • Amines Convert Esters into Amides • Benzylic Oxidation • Birch Reduction • Birch Reduction of Benzene • Blanc Chloromethylation • Bouveault-Blanc Reduction • Catalytic Hydrogenation • Claisen Condensations Produce β-Dicarbonyl Compounds • Claisen Condensations Produce β-Dicarbonyl Compounds • Complete Benzylic Oxidations of Alkyl Chains • Complete Benzylic Oxidations of Alkyl Chains • Complex Metal Hydride Reductions • Conversion of Amino with Nitro • Convert Esters into Aldehydes Using a Milder Reducing Agent • Decarboxylation of 3-Ketoacids Yields Ketones • Deprotection of Cbz-Amino Acids • Deprotonation of Methylbenzene • Directing Electron-Donating Effects of Alkyl • Electrophilic Chloromethylation of Polystyrene • Ester Cleavage • Ester Hydrolysis • Friedel-Crafts Alkylation of Benzene with Acyl Chlorides • Friedel-Crafts Alkylation of Benzene with Carboxylic Anhydrides • Friedel-Crafts Alkylation Using Alkenes • Friedel-Crafts Alkylations of Benzene Using Alkenes • Friedel-Crafts Alkylations Using Alcohols • Friedel-Crafts Reaction • Grignard Reagents Transform Esters into Alcohols • Groups that Withdraw Electrons Inductively Are Deactivating and Meta Directing • Halogenation of Benzene • Hantzsch Pyridine Synthesis • Hydrogenation to Cyclohexane • Hydrogenolysis of Benzyl Ether • Ketones Undergo Mixed Claisen Reactions to Form β-Dicarbonyl Compounds • Nitration of Benzene • Nucleophilic Aromatic Substitution • Nucleophilic Aromatic Substitution with Amine • Nucleophilicity of Sulfur Compounds • Oxidation of Alkyl-substituted Benzenes Gives Aromatic Ketones • Oxidation States of Sulfur Compounds • Preparation of Alkylbenzene • Reactions of Benzene and Substituted Benzenes • Reactions with Organometallic Reagents • Reduction of an Ester to an Alcohol • Reduction of an Ester to an Aldehyde • Reductive Removal of a Diazonium Group • Reverse Sulfonation——Hydrolysis • Specialized Acylation Reagents-Carbodiimides and Related Reagents • Sulfonation of Benzene • The Acylium Ion Attack Benzene to Form Phenyl Ketones • The Claisen Rearrangement • The Cycloaddition of Dienes to Alkenes Gives Cyclohexenes • The Nitro Group Conver to the Amino Function • Transesterification • Vilsmeier-Haack Reaction

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[ CAS No. 80-40-0 ] {[proInfo.proName]}

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[ 80-40-0 ] Synthesis Path-Upstream 1~6

[ 80-40-0 ] Synthesis Path-Downstream 1~109

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