[ CAS No. 622-24-2 ] {[proInfo.proName]}

Name: 622-24-2|(2-Chloroethyl)benzene|98%
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SKU: A317865
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3d Animation Molecule Structure of 622-24-2

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Quality Control of [ 622-24-2 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 622-24-2 ]

SDS Specification

Alternatived Products of [ 622-24-2 ]

Product Details of [ 622-24-2 ]

CAS No. :	622-24-2	MDL No. :	MFCD00000977
Formula :	C₈H₉Cl	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	MNNZINNZIQVULG-UHFFFAOYSA-N
M.W :	140.61	Pubchem ID :	231496
Synonyms :

Calculated chemistry of [ 622-24-2 ] Expand+

Physicochemical Properties

Num. heavy atoms :	9
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.25
Num. rotatable bonds :	2
Num. H-bond acceptors :	0.0
Num. H-bond donors :	0.0
Molar Refractivity :	41.01
TPSA :	0.0 Å²

Pharmacokinetics

GI absorption :	Low
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) :	-5.06 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.13
Log Po/w (XLOGP3) :	2.95
Log Po/w (WLOGP) :	2.47
Log Po/w (MLOGP) :	3.26
Log Po/w (SILICOS-IT) :	3.15
Consensus Log Po/w :	2.79

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	2.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-2.93
Solubility :	0.165 mg/ml ; 0.00117 mol/l
Class :	Soluble
Log S (Ali) :	-2.61
Solubility :	0.343 mg/ml ; 0.00244 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-3.79
Solubility :	0.0225 mg/ml ; 0.00016 mol/l
Class :	Soluble

Medicinal Chemistry

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

Safety of [ 622-24-2 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P210-P264-P273-P280-P302+P352+P332+P313+P362+P364-P305+P351+P338+P337+P313-P370+P378-P403+P235-P501	UN#:	N/A
Hazard Statements:	H227-H315-H319-H412	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 622-24-2 ]

* 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 [ 622-24-2 ]
Downstream synthetic route of [ 622-24-2 ]

[ 622-24-2 ] Synthesis Path-Upstream 1~7

1
[ 622-24-2 ]
[ 41173-70-0 ]

Reference： [1] Chemistry and Industry (London, United Kingdom), 1959, p. 657[2] Chemische Berichte, 1960, vol. 93, p. 289 Anm. 5
[3] Rev. Acad. Cienc. exact. fis. nat. Madrid, 1959, vol. 53, p. 527,543

2
[ 7446-70-0 ]
[ 622-24-2 ]
[ 107-12-0 ]
[ 41173-70-0 ]

Reference： [1] Chemistry and Industry (London, United Kingdom), 1959, p. 657[2] Chemische Berichte, 1960, vol. 93, p. 289 Anm. 5
[3] Rev.Acad.Cienc.exact.fis.nat.Madrid, 1959, vol. 53, p. 527,543

3
[ 622-24-2 ]
[ 1074-61-9 ]

Reference： [1] Journal of Organic Chemistry, 1961, vol. 26, p. 2671 - 2673

4
[ 100-41-4 ]
[ 4025-71-2 ]
[ 622-24-2 ]
[ 672-65-1 ]

Reference： [1] Journal of Organic Chemistry USSR (English Translation), 1982, vol. 18, p. 317 - 324[2] Zhurnal Organicheskoi Khimii, 1982, vol. 18, # 2, p. 365 - 373

5
[ 622-24-2 ]
[ 589-08-2 ]
[ 13977-33-8 ]

Reference： [1] Chemische Berichte, 1939, vol. 72, p. 2161,2166

6
[ 622-24-2 ]
[ 30762-06-2 ]

Reference： [1] Journal of Medicinal Chemistry, 1988, vol. 31, # 1, p. 84 - 91

7
[ 622-24-2 ]
[ 119018-29-0 ]

Reference： [1] Patent: CN107963988, 2018, A,
[2] Patent: CN107935903, 2018, A,

[ 622-24-2 ] Synthesis Path-Downstream 1~71

1
[ 109-06-8 ]
[ 622-24-2 ]
[ 2110-18-1 ]
[ 2110-16-9 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium amide

Reference： [1]Tchitchibabine [Bulletin de la Societe Chimique de France, 1938, vol. <5> 5, p. 429,432] Tchitchibabine [Bulletin de la Societe Chimique de France, 1938, vol. 5, p. 429,432]

2
[ 100-41-4 ]
[ 622-24-2 ]
[ 672-65-1 ]

Yield	Reaction Conditions	Operation in experiment
13%Spectr.; 70%	With N-chloro-succinimide; acetophenone; In acetonitrile; at 27℃; for 24h;Irradiation;	General procedure: To a 4 mL clear vial charged with the reaction substrate, N-chlorosuccinimide, ketone catalyst in anhydrous acetonitrile (0.2 M) was degassed and irradiated with a 19 W compact fluorescent lamp at room temperature for 24 h. The solvent was then removed and the residue was dissolved in diethyl ether, filtrated, concentrated and purified by preparative thin-layer chromatography.

Reference： [1]Organic and Biomolecular Chemistry,2019,vol. 17,p. 3403 - 3408
[2]Tetrahedron,2017,vol. 73,p. 3696 - 3701
[3]Monatshefte fur Chemie,1887,vol. 8,p. 104
Chemische Berichte,1893,vol. 26,p. 1707
[4]Journal of Organic Chemistry,1990,vol. 55,p. 5260 - 5269
[5]Russian Journal of Organic Chemistry,2001,vol. 37,p. 270 - 280
[6]Organic Letters,2017,vol. 19,p. 4560 - 4563

3
[ 60-12-8 ]
[ 622-24-2 ]

Yield	Reaction Conditions	Operation in experiment
95%	With 1-methyl-pyrrolidin-2-one; benzenesulfonyl chloride; In 1,2-dichloro-ethane; at 80℃; for 1.5h;	General procedure: In a round-bottom flask, benzylic alcohol 1a (10 mmol, 2.0 equiv.), benzenesulfonyl chloride 2a (13 mmol, 1.3 equiv.) and NMP (2.5 equiv.). Then, DCE (3 mL) were added. The mixture was stirred at 80 C for 1.5 h. After completion of the reaction (monitoredby TLC), water (10 mL) was added and the mixture was extracted with ethyl acetate (3*10 mL). The combined organic phase was dried over anhydrous Na2SO4, filtered, and evaporated under reduced pressure. The crude product was purified by flash chromatography on silica gel to give the desired alkyl chlorides 3.
78%	With 4-methoxy-benzoyl chloride; N,N-dimethyl-formamide; In 1,4-dioxane; at 80℃; for 3h;Sealed tube;	General procedure: Entry 1: According to general procedure II (chapter 2.1.2) 2-phenylethanol (136, 247 ilL, 252 mg, 2.00 mmol, 1.00 equiv), DMF (62 ilL, 0.80 mmol, 59 mg, 40 mol%), dioxane (1 mL, 2 M) and 4- MeOBzCI (328 ilL, 414 mg, 2.40 mmol, 1.2 equiv) were combined at ambient temperature andallowed to stir for 3 h at 80 C. ?H-N MR of the crude product (440 mg) revealed full conversion andchloride 236 to ester 336 ratio of 86:14. Finally chromatographic purification on silica gel (masscrude material/5i02 1:10) with Et20/nPen 1:99 delivered the alkyl chloride 236 as a colorless oil in 78% yield (218 mg, 1.55 mmol).
	With trichloroisocyanuric acid; In dichloromethane; at 25℃; for 0.0333333h;Sonication; Green chemistry;	General procedure: c) Dehydrohalogenation reaction using TCCA-DMFreagent under sonication: Methodology for the ultrasonicallyassisted dehydrohalogenation of alcohols by TCCA-DMF under sonication is by and large similar to the classical method. One mole of the prepared TCCA-DMF reagent and one mole of alcohol were placed in a reaction flask and clamped in a Sonicator. Progress of the reaction was checked by TLC till the completion of the reaction. After completion of the reaction as ascertained by TLC,similar work up procedure mentioned in the above section (classical method) is adopted to the alkyl chloride product. Products obtained were characterized by spectroscopic methods.

Reference： [1]Tetrahedron Letters,2006,vol. 47,p. 6821 - 6823
[2]Organic Letters,2002,vol. 4,p. 553 - 555
[3]Journal of Organic Chemistry,1998,vol. 63,p. 9565 - 9568
[4]Synthetic Communications,2018,vol. 48,p. 2793 - 2800
[5]Journal of Organic Chemistry,1995,vol. 60,p. 2638 - 2639
[6]Chemistry Letters,1984,p. 1173 - 1174
[7]Organic Letters,2014,vol. 16,p. 1720 - 1723
[8]Synthesis,1988,p. 868 - 871
[9]Canadian Journal of Chemistry,2006,vol. 84,p. 1006 - 1012
[10]Tetrahedron,2002,vol. 58,p. 8689 - 8693
[11]Journal of Organic Chemistry,1984,vol. 49,p. 3027 - 3029
[12]Patent: WO2016/202894,2016,A1 .Location in patent: Page/Page column 51; 132; 137; 162
[13]Medicinal Chemistry Research,1999,vol. 9,p. 657 - 667
[14]Synthetic Communications,1999,vol. 29,p. 1415 - 1419
[15]Chemical Communications,2019,vol. 55,p. 7962 - 7965
[16]Phosphorus, Sulfur and Silicon and the Related Elements,2006,vol. 181,p. 2445 - 2452
[17]Nature,1947,vol. 159,p. 263
[18]Journal of the Chemical Society,1949,p. 1799,1802
[19]Chemische Berichte,1929,vol. 62,p. 190
[20]Journal of the Chemical Society,1927,p. 452
[21]Journal of the Chemical Society,1953,p. 2224,2231
Journal of the Chemical Society,1954,p. Errata
[22]Zhurnal Obshchei Khimii,1959,vol. 29,p. 2631,2635; engl. Ausg. S. 2595, 2599
[23]Chemische Berichte,1912,vol. 45,p. 1268
[24]Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences,1911,vol. 152,p. 1316
[25]Journal of the Chemical Society,1909,vol. 95,p. 2196
[26]Journal of the American Chemical Society,1924,vol. 46,p. 756
[27]Journal of the Chemical Society,1954,p. 2281,2285
[28]Bulletin of the Chemical Society of Japan,1986,vol. 59,p. 3617 - 3620
[29]Canadian Journal of Chemistry,2001,vol. 79,p. 1145 - 1152
[30]Tetrahedron Letters,2007,vol. 48,p. 223 - 226
[31]Tetrahedron Letters,1985,vol. 26,p. 945 - 948
[32]Tetrahedron Letters,1985,vol. 26,p. 945 - 948
[33]Tetrahedron Letters,1985,vol. 26,p. 945 - 948
[34]Inorganic Chemistry,2010,vol. 49,p. 3261 - 3270
[35]Chemistry - A European Journal,2011,vol. 17,p. 11290 - 11295
[36]Chinese Journal of Chemistry,2012,vol. 30,p. 1647 - 1657
[37]Synthesis and Reactivity in Inorganic, Metal-Organic, and Nano-Metal Chemistry,2015,vol. 45,p. 97 - 103
[38]Angewandte Chemie - International Edition,2016,vol. 55,p. 10145 - 10149
Angew. Chem.,2016,vol. 128,p. 10300 - 10304,5
[39]Organic Letters,2018,vol. 20,p. 2468 - 2471

4
[ 34059-12-6 ]
[ 622-24-2 ]
ethyl-phenethyl-(4-phenyl-butyl)-amine [ No CAS ]

Reference： [1]Chemische Berichte,1939,vol. 72,p. 2161,2166

5
[ 996-82-7 ]
[ 622-24-2 ]
[ 6628-68-8 ]

Reference： [1]Journal of the Chemical Society,1923,vol. 123,p. 1755 - 1766

6
[ 622-24-2 ]
[ 107-06-2 ]
[ 75-36-5 ]
[ 69614-95-5 ]

Yield	Reaction Conditions	Operation in experiment
	With aluminium trichloride

Reference： [1]Baddeley et al. [Journal of the Chemical Society, 1953, p. 2110,2114]

7
[ 622-24-2 ]
[ 589-08-2 ]
[ 13977-33-8 ]

Reference： [1]Chemische Berichte,1939,vol. 72,p. 2161,2166

8
[ 622-24-2 ]
[ 71-43-2 ]
[ 1985-58-6 ]

Yield	Reaction Conditions	Operation in experiment
	With carbon disulfide; aluminium trichloride

Reference： [1]Sisido; Odazima [Kogyo Kagaku zasshi / Journal of the Society of Chemical Industry, 1942, vol. 45, p. 551][J. Soc. chem. Ind. Japan Spl., 1942, vol. 45, p. 222]

9
[ 622-24-2 ]
[ 41173-70-0 ]

Reference： [1]Chemistry and industry,1959,p. 657
Chemische Berichte,1960,vol. 93,p. 289 Anm. 5

10
[ 622-24-2 ]
[ 17376-04-4 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium iodide; In acetone; at 90℃; under 3000.3 Torr;Microwave irradiation;	A solution of 1-chloro-2-phenylethane (210 mg, 1.50 mmol) and NaI (152 mg, 1.80 mmol) in acetone (3 mL) was filled into a 10 mL-microwave pressure vial and irradiated with microwaves (program: standard; max. power 180 W; max. pressure 4 bar; temperature 90 C; time program: 5 min ramp time; 10 min hold time; 5 min cool off time). The precipitate (NaCl) was filtered off and the clear solution containing 1-iodo-2-phenylethane was treated with 4b (205 mg, 1.0 mmol), K2CO3 (1.10 g, 8.0 mmol) and a small amount of acetone (1 mL). The mixture was irradiated with microwaves (program: standard; max. power 180 W; max. pressure 4 bar; temperature 90 C; time program: 5 min ramp time; 30 min hold time; 5 min cool off time). After filtration through Celite (CH2Cl2), the solvent was removed in vacuo and the residue was purified by fc (3 cm, cyclohexane/ethyl acetate 7:3, 20 mL, Rf = 0.28). Pale yellow oil, yield 171 mg (55%). C20H23NO2 (309.4). Anal. calcd. C 77.24 H 7.56 N 4.47 found C 77.64 H 7.49 N 4.53.

Reference： [1]Journal of the American Chemical Society,1928,vol. 50,p. 1194
[2]Journal of Biological Chemistry,1915,vol. 21,p. 445
[3]Gazzetta Chimica Italiana,1960,vol. 90,p. 660 - 670
[4]European Journal of Medicinal Chemistry,2012,vol. 53,p. 327 - 336

11
[ 622-24-2 ]
[ 20264-95-3 ]

Yield	Reaction Conditions	Operation in experiment
30%	With nitric acid; at 0℃; for 0.75h;	To 1-chloro-2-phenylethane (20 g, 0.14 mol) at 0 C was added fuming nitric acid (20 ml) dropwise. The mixture was stirred at the same temperature for an additional 45 min. The reaction was quenched cautiously with water (200 mL). It was extracted with dichloromethane (100 mL), dried over MgSO4, and crystallized from chloroform/hexane to obtain 2 (8.0 g, 30 %).1H NMR (400 MHz, CDCl3) delta 8.20 (d, 2H), 7.40 (d, 2H), 3.75 (t, 2H), 3.20 (t, 2H)

Reference： [1]Patent: WO2004/26864,2004,A1 .Location in patent: Page 132; 133
[2]Zhurnal Obshchei Khimii,1959,vol. 29,p. 2631,2637;engl.Ausg.S.2595,2600
[3]Zhurnal Obshchei Khimii,1935,vol. 5,p. 1342,1344
Chemisches Zentralblatt,1936,vol. 107,p. 1534
[4]Journal of the Chemical Society,1927,p. 2232
[5]Journal of the Chemical Society,1949,p. 1799,1802
[6]Bulletin of the Chemical Society of Japan,1971,vol. 44,p. 3091 - 3095
[7]Gazzetta Chimica Italiana,1960,vol. 90,p. 660 - 670

12
[ 622-24-2 ]
[ 51-71-8 ]

Yield	Reaction Conditions	Operation in experiment
	With hydrazine
	With hydrazine hydrate In propan-1-ol Heating;
	With hydrazine hydrate In isopropyl alcohol Heating;

Reference： [1]Jensen,K.A. et al. [Acta Chemica Scandinavica (1947), 1961, vol. 15, p. 1109 - 1123]
[2]Bream,J.B. et al. [Journal of Medicinal Chemistry, 1970, vol. 13, # 6, p. 1051 - 1057]
[3]Anderson,F.E. et al. [Journal of medicinal and pharmaceutical chemistry, 1962, vol. 5, # 2, p. 221 - 230]

13
[ 100-41-4 ]
[ 4025-71-2 ]
[ 622-24-2 ]
[ 672-65-1 ]

Reference： [1]Journal of Organic Chemistry USSR (English Translation),1982,vol. 18,p. 317 - 324
Zhurnal Organicheskoi Khimii,1982,vol. 18,p. 365 - 373

14
[ 32327-70-1 ]
[ 622-24-2 ]

Yield	Reaction Conditions	Operation in experiment
85%	With palladium on activated charcoal; formic acid; N,N-dimethyl-formamide for 5h; Heating;

Reference： [1]Pandey, Paras N.; Purkayastha, Makhan L. [Synthesis, 1982, # 10, p. 876 - 878]

15
o-(N-methylcarbamoyl)phenyl 2-phenylethyl sulphoxide [ No CAS ]
[ 2527-66-4 ]
[ 622-24-2 ]

Reference： [1]Gazzetta Chimica Italiana,1987,vol. 117,p. 649 - 654

16
[ 60-12-8 ]
[ 142-62-1 ]
[ 6290-37-5 ]
[ 104-62-1 ]
[ 622-24-2 ]

Yield	Reaction Conditions	Operation in experiment
1: 26% 2: 29% 3: 39%	With pyridine; N,N-dimethylchloromethyleniminium chloride Ambient temperature;
1: 26% 2: 39% 3: 39%	With pyridine; N,N-dimethylchloromethyleniminium chloride Ambient temperature;

Reference： [1]Fujisawa, Tamotsu; Mori, Toshiki; Fukumoto, Kazumasa; Sato, Toshio [Chemistry Letters, 1982, p. 1891 - 1894]
[2]Fujisawa, Tamotsu; Mori, Toshiki; Fukumoto, Kazumasa; Sato, Toshio [Chemistry Letters, 1982, p. 1891 - 1894]

17
[ 3558-60-9 ]
[ 622-24-2 ]
[ 103-45-7 ]

Yield	Reaction Conditions	Operation in experiment
1: 20% 2: 78%	With acetyl chloride; zinc In Petroleum ether at 28℃; for 4h;

Reference： [1]Bhar, Sanjay; Ranu, Brindaban C. [Journal of Organic Chemistry, 1995, vol. 60, # 3, p. 745 - 747]

18
[ 3558-60-9 ]
[ 75-36-5 ]
[ 622-24-2 ]
[ 103-45-7 ]

Yield	Reaction Conditions	Operation in experiment
1: 78% 2: 20%	With zinc In Petroleum ether at 28℃; for 4h;

Reference： [1]Bhar, Sanjay; Ranu, Brindaban C. [Journal of Organic Chemistry, 1995, vol. 60, # 3, p. 745 - 747]

19
[ 67-56-1 ]
[ 6306-60-1 ]
[ 622-24-2 ]
[ 64008-45-3 ]

Reference： [1]Journal of Medicinal Chemistry,1977,vol. 20,p. 1511 - 1516

20
[ 6306-60-1 ]
[ 622-24-2 ]
[ 64008-66-8 ]

Reference： [1]Journal of Medicinal Chemistry,1977,vol. 20,p. 1511 - 1516

21
[ 6306-60-1 ]
[ 622-24-2 ]
[ 59666-80-7 ]

Reference： [1]Journal of Medicinal Chemistry,1977,vol. 20,p. 1511 - 1516

22
[ 622-24-2 ]
[ 38385-95-4 ]
[ 38385-99-8 ]

Reference： [1]Journal of Heterocyclic Chemistry,1995,vol. 32,p. 707 - 718

23
[ 13714-86-8 ]
[ 622-24-2 ]
1-(5-Methyl-furan-2-yl)-3,4-dihydro-isoquinoline [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
26%	With tin(IV) chloride at 110 - 115℃; for 3h;

Reference： [1]Terenin; Kontarev; Maloshitskaya; Kabanova [Chemistry of Heterocyclic Compounds, 1997, vol. 33, # 3, p. 318 - 320]

24
[ 7446-70-0 ]
[ 622-24-2 ]
[ 107-12-0 ]
[ 41173-70-0 ]

Reference： [1]Chemistry and industry,1959,p. 657
Chemische Berichte,1960,vol. 93,p. 289 Anm. 5

25
[ 622-24-2 ]
[ 107-12-0 ]
tin (II)-chloride [ No CAS ]
[ 41173-70-0 ]

Reference： [1]Chemistry and industry,1959,p. 657
Chemische Berichte,1960,vol. 93,p. 289 Anm. 5

26
[ 108-94-1 ]
[ 622-24-2 ]
[ 124620-30-0 ]

Reference： [1]Journal of the American Chemical Society,2000,vol. 122,p. 2118 - 2119
[2]Journal of the American Chemical Society,2000,vol. 122,p. 11749 - 11750
[3]Organic Letters,2003,vol. 5,p. 2041 - 2042

27
[ 505-66-8 ]
[ 622-24-2 ]
[ 40389-67-1 ]

Yield	Reaction Conditions	Operation in experiment
46%	In ethanol for 24h; Heating;

Reference： [1]Walczynski, Krzysztof; Guryn, Roman; Zuiderveld, Obbe P.; Timmerman, Henk [Il Farmaco, 1999, vol. 54, # 10, p. 684 - 694]

28
[ 622-24-2 ]
phenylmagnesium bromide [ No CAS ]
[ 103-29-7 ]

Reference： [1]Angewandte Chemie - International Edition,2002,vol. 41,p. 4056 - 4059
[2]Journal of Organometallic Chemistry,2003,vol. 687,p. 403 - 409

29
[ 622-24-2 ]
[ 443-72-1 ]
methyl-(9-phenethyl-9<i>H</i>-purin-6-yl)-amine; hydrochloride [ No CAS ]

Reference： [1]European Journal of Medicinal Chemistry,2003,vol. 38,p. 199 - 214

30
[ 60-12-8 ]
[ 98-59-9 ]
[ 4455-09-8 ]
[ 622-24-2 ]

Reference： [1]Synthetic Communications,2003,vol. 33,p. 1727 - 1732

31
[ 622-24-2 ]
[ 30762-06-2 ]

Reference： [1]Journal of Medicinal Chemistry,1988,vol. 31,p. 84 - 91

32
[ 622-24-2 ]
[ 37985-13-0 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 5 steps 1: NaOH / methanol / 5 h / Heating 2: 75 percent / 30percent H₂O₂ / acetic acid / 2 h / Heating 3: 78 percent / benzylamine, glacial acetic acid / 3 h 4: 82 percent / 2,3-dichloro-5,6-dicyanobenzoquinone (DDQ) / dioxane / 8 h / Heating 5: 72 percent / dichlorotris(triphenylphosphine)ruthenium(II), HCl gas / benzene / Heating

Reference： [1]Ramana Reddy; Manjubhashini; Reddy; Ramana Reddy; Bhaskar Reddy [Synthetic Communications, 1991, vol. 21, # 15-16, p. 1589 - 1596]

33
[ 622-24-2 ]
[ 1074-61-9 ]

Reference： [1]Journal of Organic Chemistry,1961,vol. 26,p. 2671 - 2673

34
[ 622-24-2 ]
[ 1012-05-1 ]

Reference： [1]Journal of medicinal chemistry,1968,vol. 11,p. 1258 - 1262

35
[ 622-24-2 ]
[ 1138-44-9 ]

Yield	Reaction Conditions	Operation in experiment
58%		Cyclohexylamine Compound 20a (4.64 g, 46.50 mmol) was added to a solution of cyclohexanone Compound 2a (4.0 g, 46.50 mmol) in benzene (100 mL) at ambient temperature under a N2 atmosphere. The mixture was refluxed at 80 C. for 5 hours, using a Dean Stark apparatus for the removal of water, and concentrated to dryness. The crude product was purified by distillation at aspirator pressure to afford cyclohexyl-cyclohexylidene-amine Compound 20b (7.33 g, 88%) as a clear oil. s-BuLi (28.0 mL, 1.3 M) was added slowly to a solution of Compound 20b (7.0 g) in THF (50 mL) at -78 C. The mixture stirred for 1 hr at -78 C. and then (2-chloro-ethyl)-benzene Compound 20c (5.11 g, 36.4 mmol) in THF (10 mL) was added dropwise. The reaction mixture was stirred for 24 hrs while warming to r.t. The reaction was quenched with 1N HCl (5 mL), then diluted with water (100 mL) and EtOAc (500 mL). The organic layer was washed with brine, separated and dried with anhydrous sodium sulfate, then filtered and concentrated in vacuo to yield a crude product. Purification by flash chromatography (eluted with 10% EtOAc in Hexane) afforded 2-phenethyl-cyclohexanone Compound 20d (4.05 g, 20.0 mMol, 58%) as a yellow oil. Compound 20d was carried forward in place of Compound 2a using the procedure of Example 11 to provide 2-(2,2-dimethoxy-acetyl)-6-phenethyl-cyclohexanone Compound 20e. Using the procedure of Example 10, Compound 20e was used in place of [3-(4-fluoro-benzylidene)-2-oxo-cyclohexyl]-oxo-acetic acid ethyl ester Compound 10c and (4-fluoro-phenyl)-hydrazine Compound 20f was used in place of (2,4-dichloro-phenyl)-hydrazine Compound 10d to provide 1-[1-(4-fluoro-phenyl)-7-phenethyl-4,5,6,7-tetrahydro-1H-indazol-3-yl]-2,2-dimethoxy-ethanone Compound 20g. Using the procedure of Example 11, Compound 20g was used in place of [3-(4-fluoro-benzylidene)-2-oxo-cyclohexyl]-oxo-acetic acid ethyl ester Compound 11d to provide 1-(4-fluoro-phenyl)-7-phenethyl-4,5,6,7-tetrahydro-1H-indazole-3-carbaldehyde Compound 20h. Using the procedure of Example 11, Compound 20h was used in place of 1-benzyl-4,5,6,7-tetrahydro-1H-indazole-3-carbaldehyde Compound 11e and (methylsulfonyl)(1-phenyl-ethyl)-carbamic acid tert-butyl ester Compound 20i was used in place of (methylsulfonyl)[(1R)-1-phenyl-ethyl]-carbamic acid tert-butyl ester Compound 11f to provide Compound 258. Using the procedure of Example 11, Compound 20h was used in place of 1-benzyl-4,5,6,7-tetrahydro-1H-indazole-3-carbaldehyde Compound 11e and (methylsulfonyl)(1-cyclohexyl-ethyl)-carbamic acid tert-butyl ester Compound 20j was used in place of (methylsulfonyl)[(1R)-1-phenyl-ethyl]-carbamic acid tert-butyl ester Compound 11f to provide Compound 259.

Reference： [1]Patent: US2005/228034,2005,A1 .Location in patent: Page/Page column 120-122

36
[ 845790-96-7 ]
[ 622-24-2 ]
IBI⁽⁵⁶⁰⁾S₀₀₂₈₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
85%		Example 12; Preparation of Compound 15; Compound 3 (2.10 g, 1.411 mmol) was dissolved in dry THF (70 mL) and phenethyl chloride (10 equiv) was added followed by the dropwise addition of 0.5 M KHMDS solution in toluene (1.411 mL, 0.706 mmol). The mixture was stirred for overnight at room temperature, and then deprotected according to the general procedures to provide phenethyl ether 15.

Reference： [1]Patent: WO2006/52930,2006,A1 .Location in patent: Page/Page column 51-52

37
[ 622-24-2 ]
[ 75-36-5 ]
[ 69614-95-5 ]

Yield	Reaction Conditions	Operation in experiment
	In 1,2-dichloro-ethane	1.A A. A. 4-(2-Chloroethyl)-acetophenone A solution was prepared by adding 7.11 ml (50 mmol) of acetyl chloride to a suspension of 7.34 g (55 mmol) of aluminum chloride in 35 ml of ethylene dichloride. This solution was added at room temperature to a solution of 6.58 ml (100 mmol) of phenethyl chloride in 10 ml of ethylene dichloride. The solution began to darken and give off hydrochloride and was stirred at room temperature for 25 minutes, then poured into ice and water. The layers were separated and the organic layer washed with 1N hydrochloride, saturated aqueous sodium bicarbonate solution, and brine, dried over sodium sulfate, and evaporated to an oil, which was used directly in the following reaction. NMR (CDCl3): 2.16 (s, 3H), 2.68 (m, 2H), 3.30 (m, 2H), 6.85 (d, 2H), 7.45 (d, 2H). IR (cm-1, neat): 1680 (C=O).
	In 1,2-dichloro-ethane	1.A A. A. 4-(2-Chloroethyl)-acetophenone A solution was prepared by adding 7.11 ml (50 mmol) of acetyl chloride to a suspension of 7.34 g (55 mmol) of aluminum chloride in 35 ml of ethylene dichloride. This solution was added at room temperature to a solution of 6.58 ml (100 mmol) of phenethyl chloride in 10 ml of ethylene dichloride. The solution began to darken and give off hydrochloride and was stirred at room temperature for 25 minutes, then poured into ice and water. The layers were separated and the organic layer washed with 1N hydrochloride, saturated aqueous sodium bicarbonate solution, and brine, dried over sodium sulfate, and evaporated to an oil, which was used directly in the following reaction. NMR (CDCl3): 2.16 (s, 3H), 2.68 (m, 2H), 3.30 (m, 2H), 6.85 (d, 2H), 7.45 (d, 2H). IR (cm min1, neat): 1680 (C=O).

Reference： [1]Current Patent Assignee: PFIZER INC - US4891375, 1990, A
[2]Current Patent Assignee: PFIZER INC - EP279598, 1988, A2

38
[ 75-15-0 ]
[ 622-24-2 ]
[ 100-63-0 ]
[ 1138320-45-2 ]

Yield	Reaction Conditions	Operation in experiment
86%		To a solution of substituted hydrazine (3 mmol) and carbon disulfide (8 mmol) Triton-B (2 mmol) were slowly added while stirring at room temperature. The stirring was continued till 0.5 h after which required amount of alkyl halide (3 mmol) was added (Scheme-I). The reaction was further continued until the completion of reaction (Table-1) under argon. The obtained mixture was poured into water (20 mL) and the extraction of organic layer was done with EtOAc (3 × 10 mL). The organic layer was washed with 0.1 N hydrochloric acid (20 mL), sodium bicarbonate solution (25 mL), brine solution (30 mL) and dried sodium sulfate and concentrated to get the desired compound I. Later, the desired compounds were confirmed by IR, NMR and elemental analysis.

Reference： [1]Monatshefte fur Chemie,2008,vol. 139,p. 1033 - 1036
[2]Asian Journal of Chemistry,2019,vol. 31,p. 1581 - 1584

39
[ 616-47-7 ]
[ 622-24-2 ]
1-methyl-3-(2-phenylethyl)-1H-imidazolium chloride [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
80%	at 70 - 90℃; for 1h;	2-Chloroethylbenzene (0.4 mol) was dropped into methylimidazole (0.4 mol), stirred at 70 C. The light-brown mixture was stirred for 1 h at 90 C. The crude product, in the form of a light-brown viscous oil, was cooled to room temperature and washed using 30 cm3 diethyl ether. [Ph-C2mim]Cl, 1-(2-phenylethyl)-3-methylimidazolium chloride crystallized. It was further purified by diethyl ether (4 × 30 cm3) and hexane (4 × 50 cm3) in a Schlenk apparatus. The product obtained was in the form of an off-white powder with 80% yield.

Reference： [1]ChemSusChem,2016,vol. 9,p. 2089 - 2096
[2]Journal of Molecular Liquids,2013,vol. 177,p. 85 - 93
[3]Canadian Journal of Chemistry,2009,vol. 87,p. 1650 - 1655

40
[ 622-24-2 ]
[ 105-53-3 ]
[ 6628-68-8 ]

Reference： [1]Inorganic Chemistry,2010,vol. 49,p. 3261 - 3270

41
[ 4769-96-4 ]
[ 622-24-2 ]
[ 915037-33-1 ]

Yield	Reaction Conditions	Operation in experiment
76%		To an ice cold solution of 6-nitroindole (250 mg, 1.54 mmol) in DMF (8 mL) was added sodium hydride (60% in oil suspension; 68 mg, 1.70 mmol) in one portion. The resulting dark red solution was stirred at this temperature for 30 minutes and then (2-chloro-ethyl)-benzene (0.60 mL, 2.31 mmol) was added. The reaction mixture was then heated to 110 C. for 5 hours. At this time, potassium carbonate (426 mg, 3.08 mmol) was added followed by additional 2-chloroethylbenzene (0.30 mL, 2.31 mmol) and the mixture heated at 110 C. for 17 hours. The mixture was then removed from the bath and diluted with water (20 mL) and extracted with ethyl acetate (100 mL). The organic layer was separated, washed with brine, and dried over magnesium sulfate, filtered, and concentrated to afford a brown residue. The residue was subjected to silica gel column chromatography using a ethyl acetate/hexanes (10%:90%) to provide compound 25 (310 mg, 76% yield); 1H NMR (DMSO d6) delta: 8.42 (s, 1H), 7.88 (dd, 1H, J=1.5, 8.9), 7.71-7.69 (m, 2H), 7.24-7.16 (m, 5H), 6.61 (d, 1H, J=2.8), 4.60 (t, 2H, J=7.0), 3.10 (t, 2H, J=7.0).

Reference： [1]Patent: US2006/258721,2006,A1 .Location in patent: Page/Page column 45

42
[ 17376-04-4 ]
[ 38841-98-4 ]
[ 100-42-5 ]
[ 544-76-3 ]
[ 1083-56-3 ]
[ 104-72-3 ]
[ 622-24-2 ]

Yield	Reaction Conditions	Operation in experiment
1: 29 %Chromat. 2: 23 %Chromat. 3: 20 %Chromat. 4: 16% 5: 13 %Chromat.	With C₃₂H₃₀ClN₂NiP In tetrahydrofuran; N,N-dimethyl acetamide at -20℃; for 0.5h; Inert atmosphere;

Reference： [1]Ren, Peng; Vechorkin, Oleg; Von Allmen, Kim; Scopelliti, Rosario; Hu, Xile [Journal of the American Chemical Society, 2011, vol. 133, # 18, p. 7084 - 7095]

43
[ 622-24-2 ]
[ 92039-54-8 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: 140 °C 2: methanol; sodium tetrahydroborate / 4 h / 0 °C

Reference： [1]Wichitnithad, Wisut; McManus, Terence J.; Callery, Patrick S. [Rapid Communications in Mass Spectrometry, 2010, vol. 24, # 17, p. 2547 - 2553]

44
3-methoxy-3,4-dihydrospiro[[2]benzopyran-1,3'-pyrrolidine] [ No CAS ]
[ 622-24-2 ]
3-methoxy-1'-(2-phenylethyl)-3,4-dihydrospiro[[2]benzopyran-1,3'-pyrrolidine] [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
45%	With potassium carbonate; In acetonitrile; at 140℃; under 3750.38 Torr;Microwave irradiation;	1-Chloro-2-phenylethane (57.0 mg, 0.41 mmol) and K2CO3 (298 mg, 2.16 mmol) were added to a solution of the secondary amine 3b (58.6 mg, 0.27 mmol) in acetonitrile (10 mL). The mixture was filled into a 10 mL-microwave pressure vial and irradiated with microwaves (program: standard; max. power 180 W; max. pressure 5 bar; temperature 140 C; time program: 5 min ramp time; 25 min hold time; 5 min cool off time). The mixture was filtered through Celite, washed with CH2Cl2, concentrated in vacuo and the residue was purified by fc (1 cm, petroleum ether/ethyl acetate 7:3, 5 mL, Rf = 0.22). Pale yellow oil, yield 40 mg (45%). C21H25NO2 (323.4). Anal. calcd. C 77.99 H 7.79 N 4.33 found C 77.73 H 7.85 N 4.24. MS (EI): m/z = 292 [M+ - OCH3], 232 [M+ - CH2Ph]. IR: (cm-1) = 2939 (nu C-H), 1076 (nu C-O), 752/698 (delta C-H monosubst. benzene). 1H NMR (CDCl3): delta (ppm) = 2.11-2.20 (m, 0.5H, CH2CH2N (cis or trans)), 2.29-2.46 (m, 1.5H, CH2CH2N (cis, trans)), 2.77-3.06 (m, 9H, N(CH2)2Ph (4H), CH2CH2NCH2 (4H), ArCH2CHOCH3 (1.5H; cis, trans)), 3.19-3.24 (m, 0.5H, ArCH2CHOCH3), 3.53/3.54 (2s, together 3H, OCH3 (cis, trans)), 4.80-4.85 (m, 1H, ArCH2CHOCH3), 7.03-7.08 (m, 1H, arom. H), 7.15-7.39 (m, 8H, arom. H). Ratio of diastereomers 52:48.

Reference： [1]European Journal of Medicinal Chemistry,2012,vol. 53,p. 327 - 336

45
[ 20020-27-3 ]
[ 622-24-2 ]

Reference： [1]Synlett,2012,vol. 23,p. 2692 - 2698,7

46
[ 2743-00-2 ]
[ 622-24-2 ]
[ 19946-98-6 ]

Yield	Reaction Conditions	Operation in experiment
73%	With neopentylmagnesium bromide; cobalt(II) bromide; 1,3-diisopropyl-1H-benzo[d]imidazol-3-ium bromide; In tetrahydrofuran; at 20℃; for 24h;Schlenk technique;	General procedure: A 10 mL Schlenk tube was charged with CoBr2 (6.6 mg, 0.03mmol), 1,3-diisopropyl-1H-benzimidazol-3-ium bromide (L4; 8.5mg, 0.03 mmol), 4-methoxy-N-[(1E)-1-phenylethylidene]aniline(1a, 67.6 mg, 0.30 mmol), 1-chlorooctane (2a, 76.5 muL, 0.45 mmol), and THF (0.69 mL). A 1.92 M solution of t-BuCH2MgBr inTHF (0.31 mL, 0.60 mmol) was added dropwise at 0 C, and themixture was stirred at r.t. for 6 h. The reaction was quenched by theaddition of 3 M aq HCl (1.0 mL), and the mixture was stirred at r.t.for 1 h, then extracted with EtOAc (3 × 10 mL). The organic layerswere combined, dried (MgSO4), and concentrated under reduced pressure. The crude product was purified by chromatography [silicagel, hexane-EtOAc (40:1)].

Reference： [1]Journal of the American Chemical Society,2013,vol. 135,p. 9279 - 9282
[2]Synthesis,2014,vol. 46,p. 2024 - 2039

47
[ 109-04-6 ]
[ 622-24-2 ]
[ 58086-71-8 ]

Yield	Reaction Conditions	Operation in experiment
77%	With 1,1'-bis-(diphenylphosphino)ferrocene; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; Sodium thiosulfate pentahydrate; caesium carbonate; In ethylene glycol; dimethyl sulfoxide; at 120℃;Inert atmosphere;	Under a nitrogen atmosphere, in 25 ml substrate is added into the test tube reactor 3anm (0.2mmol, 31.4 mg), 2-chloro ethyl benzene (3.0mmol, 420.0 mg), PdCl2(dppf) (0.02mmol, 14.6 mg), DPPF (0.01mmol, 5.6 mg), Cs2CO3(0.3mmol, 195.0 mg), Na2S2O35H2O (0.5mmol, 248.0 mg) DMSO (4.0 ml) and glycol (0.1 ml). Heating the reaction system to 120 C for reaction. TLC detection after the reaction is ended, the system is cooled to room temperature. Hydrosolvent quenching reaction with saturated ammonium chloride, extracted with ethyl acetate (3*10 ml), column chromatography purification to obtain the product 3an (77%).

Reference： [1]Organic Letters,2014,vol. 16,p. 1212 - 1215
[2]Patent: CN103848767,2016,B .Location in patent: Paragraph 0167-0170

48
[ 1615-14-1 ]
[ 622-24-2 ]
[ 1621086-58-5 ]

Reference： [1]ChemSusChem,2014,vol. 7,p. 1647 - 1654

49
[ 622-24-2 ]
[ 56751-12-3 ]

Reference： [1]ChemBioChem,2014,vol. 15,p. 2443 - 2449
[2]ChemBioChem,2014,vol. 15,p. 2443 - 2449
[3]Green Chemistry,2019,vol. 21,p. 4324 - 4328

50
[ 14159-55-8 ]
[ 622-24-2 ]
2-(2-phenethylcyclohex-1-en-1-yl)pyridine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
66%	With N,N,N,N,-tetramethylethylenediamine; neopentylmagnesium bromide; cobalt(II) bromide; 1,3-diisopropyl-1H-benzo[d]imidazol-3-ium bromide; In tetrahydrofuran; at 0 - 20℃; for 12h;Schlenk technique;	General procedure: General Procedure: In a 10 mL Schlenk tube were placed CoBr2 (0.3 M in THF, 0.10 mL, 0.030mmol), 1,3-diisopropylbenzimidazolium bromide (L2, 8.5 mg, 0.030 mmol), 2-alkenylpyridine(0.30 mmol), alkyl chloride (0.45 mmol), N,N,N,?N?-tetramethylethylenediamine (90 muL, 0.60mmol) and THF (0.28 mL). To the mixture was added a THF solution of tBuCH2MgBr (0.96 M,0.63 mL, 0.60 mmol) dropwise at 0 C. The resulting mixture was stirred at room temperature for12 h, and then quenched by the addition water (1.0 mL). The organic layer was separated, and the aqueous layer was extracted with ethyl acetate (3 x 3 mL). The combined organic layer was dried over Na2SO4 and concentrated under reduced pressure. The crude product was purified by silicagel chromatography to afford the alkylation product.

Reference： [1]Synlett,2015,vol. 26,p. 340 - 344

51
[ 1003-31-2 ]
[ 622-24-2 ]
[ 92059-63-7 ]

Reference： [1]MedChemComm,2015,vol. 6,p. 1679 - 1686

52
[ 622-24-2 ]
[ 98-88-4 ]
[ 94-47-3 ]

Yield	Reaction Conditions	Operation in experiment
87%	With dmap; caesium carbonate; at 50℃; for 24h;	In a 35 mL reaction tube were successively added 0.5 mmol of benzoyl chloride, 0.35 mmol of Cs2CO3, 2 mol% of DMAP and 2.5 mmol of (2-chloroethyl) benzene. The reaction system was stirred at 50 C for 24 h and then subjected to column chromatography (ethyl acetate / n-hexane = 1: 50-1: 10). The yield of phenylethyl benzoate was 87% (98.4 mg).

Reference： [1]Organic Letters,2015,vol. 17,p. 5172 - 5175
[2]Patent: CN106810444,2017,A .Location in patent: Paragraph 0018; 0019; 0020

53
methyl 5-amino-2-(phenylsulfonamido)benzoate [ No CAS ]
[ 622-24-2 ]
methyl 5-(phenethylamino)-2-(phenylsulfonamido)benzoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
85%	With potassium carbonate; In N,N-dimethyl-formamide; at 120℃; for 16h;Inert atmosphere;	methyl 5-(phenethylamino)-2-(phenylsulfonamido)benzoate (13) To a round-bottom-flask under nitrogen methyl 5-amino-2-(phenylsulfonamido)benzoate 12 (184 mg, 0.6 mmol, 1.0 equiv.) and dry DMF (20 mL) were added. This was followed by addition of K2CO3 (691 mg, 3 mmol, 5.0 equiv.) and 1 -(2-chloroethyl)benzene (0.199 mL, 211 mg, 1.5 mmol, 2.5 equiv.) and the mixture was heated at 120 C for 16 hours. The reaction mixture was then allowed to cool down to room temperature and diluted with ice H20 (20 mL). The resulting mixture was extracted with Et^O (2 x 30 mL). All the organic extracts were combined, dried over NaS04 and concentrated. The crude product was purified by flash column chromatography (ethyl acetate:hexanes=50:50) on silica gel to afford 13 (211 mg, 85%) as yellow oil. lH NMR (400 MHz, CDC13) delta 7.62-7.12 (m, 11H), 6.71-6.64 (m, 2H), 3.92-3.69 (m, 6H), 3.03-2.85 (m, 2H); 1 C NMR (100 MHz, CDC13) delta 166.57, 146.52, 139.75, 138.58, 133.08, 132.16, 131.83, 128.78, 128.64, 128.41, 127.73, 127.38, 126.31, 117.75, 117.00, 53.61, 52.04, 35.58.

Reference： [1]Journal of Medicinal Chemistry,2020,vol. 63,p. 2489 - 2510
[2]Patent: WO2016/172218,2016,A1 .Location in patent: Page/Page column 75-76

54
C₁₁H₉N₅O [ No CAS ]
[ 622-24-2 ]
C₁₉H₁₇N₅O [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate; In N,N-dimethyl-formamide; at 25℃;	To the reaction flask by adding material five, substance six, dimethyl formamide, potassium carbonate, reaction, Cooled to 25 C, The reaction solution was added to ice water, The mass of the ice water was 10 times of that of the reaction solution, filter, Washed, Drying, Substance seven was obtained
	With potassium carbonate; In N,N-dimethyl-formamide; at 80℃; for 4h;	The substance five,Substance six,Potassium carbonate,The molar ratio of dimethylformamide was 1: 1: 1: 10,The temperature was raised to 80 C for 4 hours.
	With potassium carbonate; In N,N-dimethyl-formamide; at 80℃; for 4h;	To the reaction flask was added substances five, six substances, dimethylformamide, potassium carbonate, the reaction was cooled to 25 , the reaction mixture was added to ice water, ice-water is 10 times the mass of the reaction liquid was filtered, washed with water, Dry matter seven. The molar ratio of the substance five, substance six, potassium carbonate and dimethylformamide was 1: 1: 1: 10, and the temperature was raised to 80 C for 4 hours

	With potassium carbonate; In N,N-dimethyl-formamide; at 25 - 80℃; for 4h;	the reaction bottle to add the material five, six, dimethylformamide, potassium carbonate, the reaction, cooling to 25 , the reaction solution added to the ice water, the quality of ice water as the reaction solution 10 times , Filter, washed, dried material seven. The molar ratio of the substance 5, the substance 6, the potassium carbonate and the dimethyl formamide was 1: 1: 1: 10, and the temperature was raised to 80 C for 4 hours.
	With potassium carbonate; In N,N-dimethyl-formamide;	Add substance to the reaction flask Fifth, the material six, dimethylformamide,Potassium carbonate, the reaction was cooled to 25 C, the reaction was added to ice water, the quality of ice water was 10 times the reaction mixture, filtered, washed with water, and dried to give substance seven.

Reference： [1]Patent: CN106214681,2016,A .Location in patent: Paragraph 0010; 0045; 0050; 0053-0058
[2]Patent: CN106220632,2016,A .Location in patent: Paragraph 0082; 0084; 0089; 0095
[3]Patent: CN106243058,2016,A .Location in patent: Paragraph 0108; 0114
[4]Patent: CN106333949,2017,A .Location in patent: Paragraph 0096; 0102
[5]Patent: CN106188070,2016,A .Location in patent: Paragraph 0083; 0088

55
[ 622-24-2 ]
[ 86-93-1 ]
[ 295360-72-4 ]

Yield	Reaction Conditions	Operation in experiment
81%	With tetra-(n-butyl)ammonium iodide; potassium carbonate; In 1,4-dioxane; acetonitrile; at 60℃; for 24h;	General procedure: : .. -Entry 1 According to general procedure IV (chapter 2 2 1) 2phenylethanol 136(123 ilL, 121 mg, 1.00 mmol, 1.0 equiv), FPyr (19.7 ilL,20.4 mg, 0.20 mmol, 20 mol%), dioxane (0.5 mL, 2 M) and benzoylchloride (141 ilL, 170 mg, 1.20 mmol, 1.2 equiv) were combined atambient temperature and then heated to 80 C for 2 h. Then thereaction solution was diluted with MeCN (1.5 mL, dioxane/MeCN 1:3,0.5 M), K2C03 (320 mg, 2.30 mmol, 2.3 equiv), TBAI (38 mg, 0.10 mmol, 10 mol%) and the 5-thio-1-phenyltetrazol (232 mg, 1.30 mmol, 1.3 equiv) were added and the resulting suspension was stirred for 24 h at 60 C. ?H-N MR of the crude material (375 mg) showed full conversion of the intermediate chloride 236 and a ether 43611 to ester 336 ratio of 87:13. In the following the crude material was adsorbed on silica gel (mass of crude product/Si02 1:2) through dissolution in DCM, addition of SiO2 and concentration under reduced pressure. This mixture was subjected to chromatographic purification on silica gel (mass of crude product/Si02 1:30) withEt20/DCM/nPen 5:20:65. After drying in high vacuum under stirring for 1 h the thioether 436h was isolated as a pale yellow oil in 81% yield (229 mg, 0.811 mmol).

Reference： [1]Patent: WO2016/202894,2016,A1 .Location in patent: Page/Page column 56; 150; 162; 163

56
[ 100-41-4 ]
[ 1074-11-9 ]
[ 622-24-2 ]
[ 672-65-1 ]

Yield	Reaction Conditions	Operation in experiment
19%Spectr.; 7%Spectr.; 72%	With N-chloro-succinimide; benzophenone; In acetonitrile; at 27℃; for 24h;Irradiation;Catalytic behavior;	General procedure: To a 4 mL clear vial charged with the reaction substrate, N-chlorosuccinimide, ketone catalyst in anhydrous acetonitrile (0.2 M) was degassed and irradiated with a 19 W compact fluorescent lamp at room temperature for 24 h. The solvent was then removed and the residue was dissolved in diethyl ether, filtrated, concentrated and purified by preparative thin-layer chromatography.

Reference： [1]Tetrahedron,2017,vol. 73,p. 3696 - 3701

57
[ 59-49-4 ]
[ 622-24-2 ]
3-phenethylbenzo[d]oxazol-2(3H)-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
86%		General procedure: One of 4a-d (1 equiv.) and K2CO3 (3 equiv.) in DMF was stirred at 90C for 1h, then the solution was allowed to cool to 60C and was added different substituted benzyl chlorides or phenyl ethyl chlorides (3 equiv.). The reaction mixture was stirred at 60C for another 7h and allowed to cool to room temperature. The saturated NH4Cl solution was added to quench the reaction. The mixture was diluted with water and extracted with ethyl acetate to afford the crude product that was purified by flash column chromatography on silica gel to yield the target products.4.1.5.1 3-Phenethylbenzo[d]oxazol-2(3H)-one (7a) [39] (0039) White solid. Yield 86%. Mp 116-118C. 1H NMR (300MHz, Chloroform-d): delta(ppm) 7.29 (d, J=7.7Hz, 3H), 7.20 (s, 3H), 7.10 (t, J=5.9Hz, 2H), 6.79 (d, J=7.1Hz, 1H), 4.06 (t, J=7.4Hz, 2H), 3.08 (t, J=7.2Hz, 2H). MS (EI): m/z 240.3 [M+H]+. IR (KBr): 3061, 1767, 1614, 1489, 1258cm-1.

Reference： [1]European Journal of Medicinal Chemistry,2017,vol. 138,p. 199 - 211

58
[ 622-24-2 ]
[ 95-25-0 ]
5-chloro-3-phenethylbenzo[d]oxazol-2(3H)-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
88%		General procedure: One of 4a-d (1 equiv.) and K2CO3 (3 equiv.) in DMF was stirred at 90C for 1h, then the solution was allowed to cool to 60C and was added different substituted benzyl chlorides or phenyl ethyl chlorides (3 equiv.). The reaction mixture was stirred at 60C for another 7h and allowed to cool to room temperature. The saturated NH4Cl solution was added to quench the reaction. The mixture was diluted with water and extracted with ethyl acetate to afford the crude product that was purified by flash column chromatography on silica gel to yield the target products.

Reference： [1]European Journal of Medicinal Chemistry,2017,vol. 138,p. 199 - 211

59
[ 622-24-2 ]
[ 829-85-6 ]
[ 5952-49-8 ]

Yield	Reaction Conditions	Operation in experiment
85%	Stage #1: diphenylphosphane With [iPr(Me₃Si)NC(NiPr)N(CH₂)₃NC(NiPr)N(SiMe₃)iPr]Eu}₂ at 20℃; for 0.166667h; Glovebox; Inert atmosphere; Stage #2: 2-phenylethyl chloride at 60℃; for 6h; Inert atmosphere; Glovebox;	2 [iPr(Me₃Si)NC(NiPr)N(CH₂)₃NC(NiPr)N(SiMe₃)iPr]Eu}₂ catalyzes the synthesis of alkyl phosphines with styrene and diphenylphosphine In a glove box, add the catalyst to the reaction flask{(i) (Ni3) iPr] Eu} 2 (0.01 mmol, 0.0124 g); and then adding a diphenylphosphine(0.14 mL, 1 mmol) and then stirred at room temperature for 10 min. After addition of styrene (0. 114 mL, 1 mmol) with a syringe. After 6 h of reaction at 60 ° C, Cl3 dubbed the solution. The calculated 1H spectrum yield was 96%. The remaining liquid was dissolved in an appropriate amount of ethyl acetate and the solvent was removed by rotary distillation. The solid was separated on silica gel using ethyl acetate / petroleum ether as eluent to give the corresponding alkyl phosphines, C6H4CH2CH2PPh2, 0.2468 g, 85% yield.

Reference： [1]Current Patent Assignee: SOOCHOW UNIVERSITY (SUZHOU) - CN105237555, 2017, B Location in patent: Paragraph 0028; 0029

60
2-mercapto-5-(1-phenazinyl)-1,3,4-oxadiazole [ No CAS ]
[ 622-24-2 ]
2-(phenazin-1-yl)-5-(phenethylthio)-1,3,4-oxadiazole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
35.5%	With potassium carbonate; In water; at 60℃; for 4h;	A 150 mL single-necked reaction flask was charged with 1.0 g (3.57 mmol) of 2-mercapto-5- (1-phenazinyl) -1,3,4-oxadiazole,0.6 g (4.29 mmol) of phenethyl chloride,2.0 g of potassium carbonate and 100 mL of water,The reaction was stirred at 60 4h,Dot board monitoring,The reaction is complete.filter,The filter cake was washed 1-2 times with water to obtain a crude product,Purification by column chromatography (petroleum ether: ethyl acetate = 5: 3) gave pure product,Yield 35.5%.
35.5%	With potassium carbonate; In water; at 20℃; for 4h;	General procedure: 3.6 mmol of 2-mercapto-5-(1-phenazine)-1,3,4-oxadiazole was dissolved in 100 mL of waterand added 2g of potassium carbonate. Then 3.6 mmol of the corresponding chlorine substitutedcompound was dropped in slowly. The reaction was stirred at room temperature for 4 h. Themixture was filtered, and filter cake was washed with water one to two times. Generally, theafforded crude was purified by silica column chromatography (petroleum ether : ethyl acetate = 5 :2) to give pure compound 6a - 6p (Sudha et al. 2017).

Reference： [1]Patent: CN107382988,2017,A .Location in patent: Paragraph 0050; 0051; 0052; 0053
[2]Natural Product Research,2019,vol. 33,p. 2145 - 2150

61
[ 532-27-4 ]
[ 622-24-2 ]

Yield	Reaction Conditions	Operation in experiment
85%	With titanium tetrachloride; In 1,2-dichloro-ethane; for 3h;Reflux;	General procedure: A solution of 2-chloro-1-[4-(propan-2-yl)phenyl]ethanone (1 g, 5.1 mmol) in dichloroethane (DCE) (10 mL) was placed in a 50 mLthree-mouth round-bottomed flask equipped with a reflux condenser, a calcium chloride drying tube, a thermometer and a magnetic stirring bar. To the stirred reaction solution at room temperature, tickle (0.115 mL, 25%) followed by PMHS (0.7 g, 12.2 mmol) were added from a syringe. The reaction mixture was heated to reflux and progress of the reaction monitored by thin layer chromatography (tlc) and stopped after three hours. The gelatinous reaction mixture was taken up in hexane (15 mL) and filtered under a plug of celite. The filter cake was washed with hexane (50 mL) and the filtrate concentrated in vacuo.

Reference： [1]Bulletin of the Chemical Society of Ethiopia,2018,vol. 32,p. 179 - 184

62
3-ethyl-4-methyl-2-oxo-3-pyrroline-1-carboxamide [ No CAS ]
[ 622-24-2 ]
[ 247098-18-6 ]

Yield	Reaction Conditions	Operation in experiment
85.24%	With copper(l) iodide; sodium hydroxide; In Petroleum ether; at 85℃; for 9h;	3-Ethyl-4-methyl-2-oxo-3-pyrroline-1-carboxamide (A) (35 g, 2.1 mol) and (2-chloroethyl)benzene (B) (32.8 g, Mix 2.52 mol) and add 50% sodium hydroxide solution (55ml),In a flask of a mixture of petroleum ether (72 ml) and copper iodide (5.07 g, 0.78 mol), the reaction was carried out at 85C for 9 hours. After the reaction was completed, the temperature was lowered to 6C to obtain of 3-ethyl-4-methyl-2-oxo-N-(2-phenylethyl)-2,5-dihydro-1H-pyrrole-1-carboxamide (C) (53.8 g) in a yield of 85.24%.Purity is 99.78%.
85.24%	With copper(l) iodide; sodium hydroxide; In Petroleum ether; at 85℃; for 9h;	3-Ethyl-4-methyl-2-oxo-3-pyrroline-1-carboxamide (A) (35 g, 2.1 mol)Mixed with (2-chloroethyl)benzene (B) (32.8 g, 2.52 mol) and added to 50% sodium hydroxide solution (55 ml),In a flask of a mixture of petroleum ether (72 ml) and copper iodide (5.07 g, 0.78 mol), the reaction was carried out at 85C for 9 hours.After the reaction was completed, the temperature was lowered to 6C to obtain 3-ethyl-4-methyl-2-oxo-3-pyrroline-1-(N-phenethyl)-formamide (C) (53.8 g).The yield was 85.24% and the purity was 99.78%.

Reference： [1]Patent: CN107963988,2018,A .Location in patent: Paragraph 0005; 0013-0014
[2]Patent: CN107935903,2018,A .Location in patent: Paragraph 0014; 0015

63
[ 622-24-2 ]
[ 119018-29-0 ]

Reference： [1]Patent: CN107963988,2018,A
[2]Patent: CN107935903,2018,A

64
[ 622-24-2 ]
[ 24521-76-4 ]
6-(phenethylthio)-1H-pyrazolo[3,4-d]pyrimidin-4-ol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
76%		To a stirred solution of 6-mercapto-1H-pyrazolo[3,4-d]pyrimidin-4-ol (compound 4, 0.3 g, 0.00179 mol) in N,N-dimethylformamide (2 mL), K2CO3 (0.247 g, 0.00179 mol) was added and stirred at room temperature for 10 min. To this constantly stirred reaction mass, 2-chloroethyl benzene (0.28 mL, 0.002 mol) was slowly added dropwise and heated at 80 C for 20 min. in a microwave reactor at 150 psi. After completion of reaction (monitoredon TLC), the reaction mixture was poured in ice cold water andextracted with dichloromethane (DCM). The extracted organiclayer was dried over anhydrous sodium sulphate and concentrated under reduced pressure to obtain crude product (dark brown viscous liquid) which was further purified by flash silica column[MeOH/ DCM, 10:90] to afford the desired compound 5a as light brown solid. Yield: 76%; mp 210-212 C; FTIR (ATR, cm1) mmax:3022 (NH Str.), 2920 (Ar-H Str. of Pyr.), 1671 (CO Str.); 1H NMR(400 MHz, DMSO-d6) d: 13.59 (s, 1H, NH), 12.22 (s, 1H, OH), 8.03(s, 1H, ArH), 7.31 (t, J = 2.52 Hz, 4H, ArH), 7.25-7.20 (m, 1H, ArH),3.41 (t, J = 5.04 Hz, 2H, CH2), 2.99 (t, J = 7.56 Hz, 2H, CH2) ppm;13C NMR (100 MHz, DMSO-d6) d: 158.20, 139.93, 128.73, 128.62,128.41, 126.41, 102.89, 34.61 (CH2), 31.08 (CH2) ppm.

Reference： [1]Bioorganic Chemistry,2018,vol. 79,p. 46 - 59
[2]Journal of Molecular Structure,2019,vol. 1183,p. 246 - 255

65
[ 574745-97-4 ]
[ 622-24-2 ]
[ 91-00-9 ]
C₃₀H₂₇N₃O₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
44.9%		2.1 g of compound 1 was dissolved into 15mL of DMF, add 1.39 g of potassium carbonate, stir at 50 C with heating, add the drops of alpha-chloroethylbenzene (1.41g), heat to reflux, and react for 3h, and then cool at 60 C, added the drops of Diphenyl methylamine (1.83g), heat again to reflux, carry on reaction for 1.5h, after the reaction, filter, filter cake washed with a small amount of DMF, the filtrate is distilled off under reduced pressure, add 15g of ice water, stir, and filter and obtained a crude product, adding the crude product to methanol and then, it is made into salt with concentrated hydrochloric acid, by filter obtained hydrochloride salt of compound I-2, hydrochloride added into 6mL of water, adjust adjusting the pH at 8 with ammonium hydroxide and obtain a large amount of white powder, filter, dry, i.e. obtained Compound I-2 (2.07g, yield 44.9%).

Reference： [1]Patent: CN108358855,2018,A .Location in patent: Paragraph 0029; 0030

66
[ 622-24-2 ]
[ 70111-05-6 ]
[ 56751-12-3 ]

Reference： [1]Green Chemistry,2019,vol. 21,p. 4324 - 4328
[2]Green Chemistry,2019,vol. 21,p. 4324 - 4328
[3]European Journal of Organic Chemistry,2020,vol. 2020,p. 821 - 825

67
N-(5-fluoro-2-(1H-pyrrol-1-yl)phenyl)-4-hydroxybenzamide [ No CAS ]
[ 622-24-2 ]
N-(5-fluoro-2-(lH-pyrrol-1-yl)phenyl)-4-phenethoxybenzamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
69%	With potassium carbonate; In N,N-dimethyl-formamide; at 90℃; for 2h;	General procedure: To a solution of compound 6 (0.06mmol) in 2 ml DMF was added potassium carbonate (0.18 mmol). The mixture was heated to 90 C and l-(2- chloroethyl)piperidine hydrochloride (0.066 mmol) was added. The reaction mixture was then stirred at 90 C for two hours. After the reaction was completed, the mixture was poured into 50 ml water and then extracted with dichloromethane (50 ml x 3). The organic layer was dried with anhydrous Na2S04 and evaporated to dryness under reduced pressure to give the crude product, which was further purified by flash silica gel column chromatography (methanol : dichloromethane = 1:12) to give a light yellow paste (yield 63%).

Reference： [1]Patent: WO2019/165158,2019,A1 .Location in patent: Page/Page column 74; 75

68
[ 622-24-2 ]
[ 75-86-5 ]
[ 645-59-0 ]

Yield	Reaction Conditions	Operation in experiment
97.9%		General procedure: Dissolve 1.5 mol of acetone cyanohydrinIn a mixed solvent of 1,3-dimethylimidazolidinone and tetrahydrofuran (volume ratio 1:3), 1.5 mol of catalyst lithium hydroxide monohydrate was added, and after stirring at 50 C for one hour, 1 mol of benzyl bromide was added, TLC After the disappearance of the monitoring raw materials, the mixture was washed with water, extracted with ethyl acetate, and the ethyl acetate layer was washed with water and saturated brine, respectively.After drying over anhydrous Na 2 SO 4 , the mixture was filtered and concentrated to give phenylacetonitrile. The reaction time was 2.5 h, and the yield was 97%.

Reference： [1]Patent: CN110003047,2019,A .Location in patent: Paragraph 0043-0049; 0051-0057; 0059

69
[ 100-59-4 ]
[ 622-24-2 ]
[ 100-42-5 ]
[ 612-00-0 ]
[ 100-41-4 ]
[ 103-29-7 ]

Yield	Reaction Conditions	Operation in experiment
	With 1,1'-bis-(diphenylphosphino)ferrocene; [(1,1′-bis(diphenylphosphino)ferrocene)Ni⁽⁰⁾(1,5-cyclooctadiene)] In tetrahydrofuran at 85℃; for 24h;

Reference： [1]Greaves, Megan E.; Lloyd-Jones, Guy C.; Maseras, Feliu; Nelson, David J.; Ronson, Thomas O.; Sproules, Stephen [ACS Catalysis, 2020, vol. 10, # 18, p. 10717 - 10725]

70
[ 4394-85-8 ]
[ 622-24-2 ]
[ 949-01-9 ]

Yield	Reaction Conditions	Operation in experiment
78%	With sulfur; sodium hydroxide at 100℃; for 8h; Schlenk technique;

Reference： [1]Chen, Xinzhi; Ge, Xin; Jin, Hao; Qian, Chao; Zhou, Shaodong [European Journal of Organic Chemistry, 2021, vol. 2021, # 23, p. 3403 - 3406]

71
[ 2591-86-8 ]
[ 622-24-2 ]
[ 24815-46-1 ]

Yield	Reaction Conditions	Operation in experiment
70%	With sulfur; sodium hydroxide at 100℃; for 8h; Schlenk technique;

Reference： [1]Chen, Xinzhi; Ge, Xin; Jin, Hao; Qian, Chao; Zhou, Shaodong [European Journal of Organic Chemistry, 2021, vol. 2021, # 23, p. 3403 - 3406]

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Technical Information

• Acid-Catalyzed α -Halogenation of Ketones • Addition of a Hydrogen Halide to an Internal Alkyne • Alcohols from Haloalkanes by Acetate Substitution-Hydrolysis • Alkyl Halide Occurrence • Alkylation of an Alkynyl Anion • An Alkane are Prepared from an Haloalkane • Benzylic Oxidation • Birch Reduction • Birch Reduction of Benzene • Blanc Chloromethylation • Chloroalkane Synthesis with SOCI2 • Complete Benzylic Oxidations of Alkyl Chains • Complete Benzylic Oxidations of Alkyl Chains • Conversion of Amino with Nitro • Convert Haloalkanes into Alcohols by SN2 • Deprotonation of Methylbenzene • Directing Electron-Donating Effects of Alkyl • Electrophilic Chloromethylation of Polystyrene • Friedel-Crafts Alkylation of Benzene with Acyl Chlorides • Friedel-Crafts Alkylation of Benzene with Carboxylic Anhydrides • Friedel-Crafts Alkylation of Benzene with Haloalkanes • Friedel-Crafts Alkylation Using Alkenes • Friedel-Crafts Alkylations of Benzene Using Alkenes • Friedel-Crafts Alkylations Using Alcohols • Friedel-Crafts Reaction • General Reactivity • Grignard Reaction • Groups that Withdraw Electrons Inductively Are Deactivating and Meta Directing • Halogenation of Alkenes • Halogenation of Benzene • Hiyama Cross-Coupling Reaction • Hydrogenation to Cyclohexane • Hydrogenolysis of Benzyl Ether • Kinetics of Alkyl Halides • Kumada Cross-Coupling Reaction • Methylation of Ammonia • Nitration of Benzene • Nucleophilic Aromatic Substitution • Nucleophilic Aromatic Substitution with Amine • Oxidation of Alkyl-substituted Benzenes Gives Aromatic Ketones • Preparation of Alkylbenzene • Reactions of Alkyl Halides with Reducing Metals • Reactions of Amines • Reactions of Benzene and Substituted Benzenes • Reductive Removal of a Diazonium Group • Reverse Sulfonation——Hydrolysis • Stille Coupling • Substitution and Elimination Reactions of Alkyl Halides • Sulfonation of Benzene • Suzuki Coupling • The Acylium Ion Attack Benzene to Form Phenyl Ketones • The Claisen Rearrangement • The Nitro Group Conver to the Amino Function • Vilsmeier-Haack Reaction

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H400	Very toxic to aquatic life
H401	Toxic to aquatic life
H402	Harmful to aquatic life
H410	Very toxic to aquatic life with long-lasting effects
H411	Toxic to aquatic life with long-lasting effects
H412	Harmful to aquatic life with long-lasting effects
H413	May cause long-lasting harmful effects to aquatic life
H420	Harms public health and the environment by destroying ozone in the upper atmosphere

[ CAS No. 622-24-2 ] {[proInfo.proName]}

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Product Details of [ 622-24-2 ]

Calculated chemistry of [ 622-24-2 ] Expand+

Physicochemical Properties

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Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

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Application In Synthesis of [ 622-24-2 ]

[ 622-24-2 ] Synthesis Path-Upstream 1~7

[ 622-24-2 ] Synthesis Path-Downstream 1~71

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Aryls

Chlorides

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[ 622-24-2 ]