[ CAS No. 3481-09-2 ] {[proInfo.proName]}

Name: 3481-09-2|N-Chlorophthalimide|95%
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Quality Control of [ 3481-09-2 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 3481-09-2 ]

SDS Specification

Alternatived Products of [ 3481-09-2 ]

Product Details of [ 3481-09-2 ]

CAS No. :	3481-09-2	MDL No. :	MFCD00023027
Formula :	C₈H₄ClNO₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	WDRFYIPWHMGQPN-UHFFFAOYSA-N
M.W :	181.58	Pubchem ID :	18997
Synonyms :

Calculated chemistry of [ 3481-09-2 ]

Physicochemical Properties

Num. heavy atoms :	12
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.0
Num. rotatable bonds :	0
Num. H-bond acceptors :	2.0
Num. H-bond donors :	0.0
Molar Refractivity :	46.71
TPSA :	37.38 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) :	-6.33 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.44
Log Po/w (XLOGP3) :	1.52
Log Po/w (WLOGP) :	1.06
Log Po/w (MLOGP) :	1.57
Log Po/w (SILICOS-IT) :	1.58
Consensus Log Po/w :	1.43

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	1.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-2.29
Solubility :	0.924 mg/ml ; 0.00509 mol/l
Class :	Soluble
Log S (Ali) :	-1.91
Solubility :	2.22 mg/ml ; 0.0122 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-2.68
Solubility :	0.381 mg/ml ; 0.0021 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	2.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.18

Safety of [ 3481-09-2 ]

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 [ 3481-09-2 ]

* 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 [ 3481-09-2 ]
Downstream synthetic route of [ 3481-09-2 ]

[ 3481-09-2 ] Synthesis Path-Upstream 1~15

1
[ 3481-09-2 ]
[ 7597-18-4 ]
[ 50593-68-5 ]

Yield	Reaction Conditions	Operation in experiment
89%	With hydrogenchloride In tetrahydrofuran; water	A. Preparation of 3-chloro-6-nitro-1H-indazole. To a solution of 6-nitro-1H-indazole (1.63 g, 10.0 mmol) in 15 mL of THF and 0.15 mL of 0.1N HCl was added 2-chloro-1H-isoindole-1,3(2H)-dione (1.36 g, 10.2 mmol) in portions. The reaction mixture was stirred at room temperature for 20 h. To the reaction mixture was added water (75 mL). A yellow precipitate formed which was collected by filtration, washed with 1/1 water:methanol to provided 3-chloro-6-nitro-1H-indazole (1.76 g, 89percent yield).

Reference： [1] Patent: US2002/25957, 2002, A1,

2
[ 136918-14-4 ]
[ 3481-09-2 ]

Yield	Reaction Conditions	Operation in experiment
71%	With aluminum (III) chloride; lead(IV) tetraacetate In acetonitrile at 20℃; for 20 h; Reflux; Inert atmosphere	AlCl₃ (1 eq, 10 mmol, 1.36 g) was added to a solution of Pb(OAc)₄ (1 eq, 10 mmol, 4.52 g) in dry CH₃CN (100 mL). The mixture was stirred at RT for 5 min, then phthalimide (1 eq, 10 mmol, 1.5 g) was added. The resulting mixture was gently refluxed until nitrogen for 20 h, then cooled to RT. The solvent was removed by rotary evaporation, and the crude was purified by chromatographic purification with pure DCM as eluent. Yield: 1.32 g, 71percent. ¹H NMR (300 MHz, CDCl₃): δ7.94–7.91 (m, 2H), 7.82–7.79 (m, 2H) ppm.

Reference： [1] Synthesis, 2009, # 16, p. 2797 - 2801
[2] Synlett, 2006, # 2, p. 194 - 200
[3] Catalysis Today, 2018, vol. 308, p. 94 - 101
[4] Fortschr. Teerfarbenfabr. Verw. Industriezweige, vol. 6, p. 1302
[5] Fortschr. Teerfarbenfabr. Verw. Industriezweige, vol. 8, p. 163
[6] Patent: US2472361, 1944, ,
[7] Tetrahedron Letters, 1990, vol. 31, # 6, p. 873 - 874
[8] Patent: CN108101800, 2018, A, . Location in patent: Paragraph 0016
[9] Fortschr. Teerfarbenfabr. Verw. Industriezweige, vol. 8, p. 162

3
[ 1074-82-4 ]
[ 3481-09-2 ]

Yield	Reaction Conditions	Operation in experiment
94%	With chlorine In tetrachloromethane; water	A. To 100 ml. of carbon tetrachloride saturated with chlorine at 0° C. to 5° C. were added 5 grams (27 mmoles) of potassium phthalimide. The resulting yellow-green suspension was allowed to warm to room temperature and then was stirred for 60-90 minutes. The solvent then was removed in vacuo, and about 100 ml. of water were added to the resulting white solid. The mixture was filtered, and the collected solid was washed with water and vacuum dried to obtain 4.6 grams (94percent yield) of N-chlorophthalimide.
92.5%	With acetic acid In water	EXAMPLE 6 The procedure of Example 5 was repeated using 48 grams of potassium phthalimide. The workup was modified to use dilute acetic acid (15.5 ml. glacial acetic acid in 500. m. of water) followed by a water wash. Heptane was not employed. N-chlorophthalimide (42.0 grams; 92.5percent yield) was recovered.

Reference： [1] Patent: US4082766, 1978, A,
[2] Patent: US4082766, 1978, A,
[3] Advanced Synthesis and Catalysis, 1998, vol. 340, # 2, p. 129 - 134

4
[ 33081-78-6 ]
[ 3481-09-2 ]

Reference： [1] Patent: US4082766, 1978, A,

5
[ 1074-82-4 ]
[ 3481-09-2 ]

Yield	Reaction Conditions	Operation in experiment
46.4 grams (95.% yield)	With chlorine In dichloromethane; water	EXAMPLE 5 Chlorine gas was added to one liter of methylene chloride for 20 minutes at 0° C. during which time saturation was achieved. Potassium phthalimide (50 grams; 270 mmoles) was added to the chlorine-saturated methylene chloride. Cooling was discontinued, and the mixture was stirred for two hours during which time the mixture warmed to 20° C. The resulting slightly greenish-yellow mixture was evaporated to a slush without filtering, and water was added to the mixture to dissolve the resulting potassium chloride. The total mixture was filtered, and the solid which was collected was washed with water and then with heptane. The solid was vacuum-dried overnight to obtain 46.4 grams (95.percent yield) of N-chlorophthalimide.

Reference： [1] Patent: US4082766, 1978, A,

6
[ 136918-14-4 ]
[ 3481-09-2 ]

Reference： [1] Patent: US4212977, 1980, A,

7
[ 136918-14-4 ]
[ 507-40-4 ]
[ 3481-09-2 ]

Reference： [1] Journal of the American Chemical Society, 1954, vol. 76, p. 3856

8
[ 68965-44-6 ]
[ 1074-82-4 ]
[ 3481-09-2 ]

Reference： [1] Organic Process Research and Development, 2017, vol. 21, # 9, p. 1383 - 1387

9
[ 85-44-9 ]
[ 3481-09-2 ]

Reference： [1] Patent: CN108101800, 2018, A,

10
[ 67-66-3 ]
[ 33081-78-6 ]
[ 7782-50-5 ]
[ 3481-09-2 ]

Reference： [1] Chemische Berichte, 1900, vol. 33, p. 23
[2] Fortschr. Teerfarbenfabr. Verw. Industriezweige, vol. 5, p. 149

11
[ 7732-18-5 ]
[ 33081-78-6 ]
[ 7782-50-5 ]
[ 3481-09-2 ]

Reference： [1] Chemische Berichte, 1900, vol. 33, p. 23
[2] Fortschr. Teerfarbenfabr. Verw. Industriezweige, vol. 5, p. 149

12
[ 136918-14-4 ]
[ 7732-18-5 ]
[ 13898-47-0 ]
[ 3481-09-2 ]

Reference： [1] Fortschr. Teerfarbenfabr. Verw. Industriezweige, vol. 8, p. 162

13
[ 3481-09-2 ]
[ 106-93-4 ]
[ 574-98-1 ]

Reference： [1] RSC Advances, 2015, vol. 5, # 80, p. 65600 - 65603

14
[ 110-52-1 ]
[ 3481-09-2 ]
[ 5394-18-3 ]

Reference： [1] RSC Advances, 2015, vol. 5, # 80, p. 65600 - 65603

15
[ 3481-09-2 ]
[ 531-52-2 ]
[ 298-96-4 ]

Reference： [1] Chemische Berichte, 1953, vol. 86, p. 858,860

[ 3481-09-2 ] Synthesis Path-Downstream 1~88

1
[ 67-56-1 ]
[ 3481-09-2 ]
[ 7143-42-2 ]

Reference： [1]Chemische Berichte,1900,vol. 33,p. 23
[2]Patent: DE119661,
Fortschr. Teerfarbenfabr. Verw. Industriezweige,vol. 6,p. 155

2
[ 3481-09-2 ]
[ 77383-58-5 ]
[ 141-78-6 ]
5-[2]quinolyl-2,3-diphenyl-tetrazolium; bromide [ No CAS ]

Reference： [1]Chemische Berichte,1953,vol. 86,p. 858,860

3
[ 3481-09-2 ]
[ 824-79-3 ]
[ 27722-45-8 ]

Reference： [1]Justus Liebigs Annalen der Chemie,1958,vol. 616,p. 183,206

4
[ 3481-09-2 ]
[ 124-41-4 ]
<i>N</i>-(2-methoxycarbonyl-phenylcarbamoyl)-phthalamic acid methyl ester [ No CAS ]

Reference： [1]Chemische Berichte,1900,vol. 33,p. 23

5
[ 3481-09-2 ]
[ 141-52-6 ]
[ 108890-73-9 ]

Reference： [1]Chemische Berichte,1900,vol. 33,p. 23
[2]Patent: DE119661,
Fortschr. Teerfarbenfabr. Verw. Industriezweige,vol. 6,p. 155

6
[ 3481-09-2 ]
[ 531-52-2 ]
[ 298-96-4 ]

Reference： [1]Chemische Berichte,1953,vol. 86,p. 858,860

7
[ 3481-09-2 ]
[ 118-92-3 ]

Yield	Reaction Conditions	Operation in experiment
96.4%	With sodium hydroxide; at 20℃; for 1h;	(4) After the reaction was stirred at room temperature for three hours, a solid was collected by filtration, 100 g of water was used to wash the solid, and the mother liquor was added to the next batch of the reaction solution;(5) Put the solid into 1800g liquid caustic soda Stir at room temperature for one hour. The liquid caustic soda was used as a 40% by weight sodium hydroxide solution;(6) adding hydrochloric acid to the reaction solution to adjust the PH = 3-4, precipitate a lot of solid;(7) Filter and dry the product 535g o-aminobenzoic acid, content 99.3%, yield 96.4%;The acetic acid solution used in the process can be applied, and after the application, the yield is improved and the quality is stable. The wastewater after centrifuging the product was light yellow and the COD in the wastewater was 1710.

Reference： [1]Patent: CN108101800,2018,A .Location in patent: Paragraph 0016
[2]Patent: DE133950,
Fortschr. Teerfarbenfabr. Verw. Industriezweige,vol. 6,p. 157

8
[ 96-54-8 ]
[ 3481-09-2 ]
[ 116625-46-8 ]

Reference： [1]Journal of Organic Chemistry,1989,vol. 54,p. 5347 - 5350
[2]Journal of Organic Chemistry,1989,vol. 54,p. 5347 - 5350
[3]Tetrahedron Letters,1988,vol. 29,p. 2405 - 2408

9
[ 7435-07-6 ]
[ 3481-09-2 ]
[ 122845-11-8 ]

Reference： [1]Journal of Organic Chemistry,1989,vol. 54,p. 5347 - 5350

10
[ 24764-40-7 ]
[ 3481-09-2 ]
[ 122845-08-3 ]

Reference： [1]Journal of Organic Chemistry,1989,vol. 54,p. 5347 - 5350

11
[ 635-90-5 ]
[ 3481-09-2 ]
[ 122845-02-7 ]

Reference： [1]Journal of Organic Chemistry,1989,vol. 54,p. 5347 - 5350

12
[ 2051-97-0 ]
[ 3481-09-2 ]
[ 122845-05-0 ]

Reference： [1]Journal of Organic Chemistry,1989,vol. 54,p. 5347 - 5350

13
[ 5707-04-0 ]
[ 3481-09-2 ]
[ 78488-63-8 ]

Reference： [1]Journal of Organic Chemistry USSR (English Translation),1981,vol. 17,p. 448 - 452
Zhurnal Organicheskoi Khimii,1981,vol. 17,p. 529 - 533

14
[ 3481-09-2 ]
[ 134306-60-8 ]
[ 127878-08-4 ]

Reference： [1]Tetrahedron Letters,1990,vol. 31,p. 873 - 874

15
[ 3481-09-2 ]
[ 23974-72-3 ]
[ 71098-88-9 ]

Reference： [1]Tetrahedron Letters,1990,vol. 31,p. 873 - 874

16
[ 3481-09-2 ]
[ 3682-36-8 ]
[ 80031-15-8 ]

Reference： [1]Synthesis,1981,p. 746 - 748

17
[ 3481-09-2 ]
[ 53724-36-0 ]
[ 20710-51-4 ]
[ 80031-17-0 ]

Reference： [1]Synthesis,1981,p. 746 - 748

18
[ 3481-09-2 ]
[ 68340-48-7 ]
[ 80031-21-6 ]

Reference： [1]Synthesis,1981,p. 746 - 748

19
[ 3481-09-2 ]
[ 5109-05-7 ]
[ 80031-22-7 ]

Reference： [1]Synthesis,1981,p. 746 - 748

20
[ 3481-09-2 ]
[ 68340-47-6 ]
[ 80031-20-5 ]

Reference： [1]Synthesis,1981,p. 746 - 748

21
[ 3481-09-2 ]
[ 71141-62-3 ]
[ 80031-16-9 ]

Reference： [1]Synthesis,1981,p. 746 - 748

22
[ 3481-09-2 ]
[ 80031-10-3 ]
[ 80031-19-2 ]

Reference： [1]Synthesis,1981,p. 746 - 748

23
[ 3481-09-2 ]
[ 7764-29-6 ]

Reference： [1]Journal of Organic Chemistry USSR (English Translation),1986,vol. 22,p. 86 - 92
Zhurnal Organicheskoi Khimii,1986,vol. 22,p. 100 - 106

24
[ 43036-06-2 ]
[ 3481-09-2 ]
[ 749250-52-0 ]

Reference： [1]Journal of the Indian Chemical Society,2003,vol. 80,p. 851 - 852

25
[ 3481-09-2 ]
[ 749250-53-1 ]

Reference： [1]Journal of the Indian Chemical Society,2003,vol. 80,p. 851 - 852

26
[ 3481-09-2 ]
[ 173853-60-6 ]

Reference： [1]Journal of the Chemical Society. Perkin Transactions 2 (2001),1999,p. 1433 - 1437

27
[ 3481-09-2 ]
[ 173853-65-1 ]

Reference： [1]Journal of the Chemical Society. Perkin Transactions 2 (2001),1999,p. 1433 - 1437
[2]Tetrahedron Letters,1995,vol. 36,p. 9261 - 9264

28
[ 3481-09-2 ]
[ 173853-63-9 ]

Reference： [1]Journal of the Chemical Society. Perkin Transactions 2 (2001),1999,p. 1433 - 1437

29
[ 3481-09-2 ]
[ 7597-18-4 ]
[ 50593-68-5 ]

Yield	Reaction Conditions	Operation in experiment
89%	With hydrogenchloride; In tetrahydrofuran; water;	A. Preparation of 3-chloro-6-nitro-1H-indazole. To a solution of 6-nitro-1H-indazole (1.63 g, 10.0 mmol) in 15 mL of THF and 0.15 mL of 0.1N HCl was added 2-chloro-1H-isoindole-1,3(2H)-dione (1.36 g, 10.2 mmol) in portions. The reaction mixture was stirred at room temperature for 20 h. To the reaction mixture was added water (75 mL). A yellow precipitate formed which was collected by filtration, washed with 1/1 water:methanol to provided 3-chloro-6-nitro-1H-indazole (1.76 g, 89% yield).

Reference： [1]Patent: US2002/25957,2002,A1

30
[ 6960-42-5 ]
[ 3481-09-2 ]
[ 165669-14-7 ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogenchloride; In tetrahydrofuran; water;	A. Preparation of 7-nitro-3-chloro-1H-indole. To a mixture of 7-nitro-1H-indole (2.0 g, 12.3 mmol) in THF (10 mL) and 0.1 N HCl (0.16 mL, 16 mmol) was added <strong>[3481-09-2]2-chloro-1H-isoindole-1,3(2H)-dione</strong> (1.68 g, 12.5 mmol) in one ortion. The reaction was stirred at room temperature for 5 h. Water (53 mL) was added. The resulting precipitate were collected by filtration; washed successively with water, methanol/water (1:1), and isopropyl ether; and was dried to afford the title compound 7-nitro-3-chloro-1H-indole. (1.3 g, 54%)

Reference： [1]Patent: US2002/25957,2002,A1

31
[ 3481-09-2 ]
[ 74784-70-6 ]
2-chloroamino-5-trifluoromethylpyridine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In toluene;	EXAMPLE 9 Into the same 300 ml four-necked flask as used in Example 1, 16.2 g (0.1 mol) of 2-amino-5-trifluoromethylpyridine, 20.9 g (0.115 mol) of <strong>[3481-09-2]N-chlorophthalimide</strong> and 150 g of toluene were added, and the reaction was carried out at 80 C. for one hour under heating with stirring. During the reaction, formation of 2-chloroamino-5-trifluoromethylpyridine was confirmed.

Reference： [1]Patent: US5491239,1996,A

32
disodium hydrogenphosphate [ No CAS ]
[ 3481-09-2 ]
p-Nitrobenzyl 6-phenoxy acetamido penam-3-carboxylate-1-oxide [ No CAS ]
[ 78183-91-2 ]

Yield	Reaction Conditions	Operation in experiment
10.35 g (96.9%)	In toluene;	EXAMPLE 2 p-nitrobenzyl-3-methyl-2-(2-chlorosulfinyl-4-oxo-3-phenoxy acetamido-1-azetidinyl)-3-butenoate Toluene 300 ml was distilled under a Dean Stark water trap till 80 ml of liquid was removed. 2.9 g of disodium hydrogen orthophosphate, 10 g of p-Nitrobenzyl 6-phenoxy acetamido penam-3-carboxylate-1-oxide and 5.0 g of <strong>[3481-09-2]N-chlorophthalimide</strong> were added. The suspension was heated at the reflux temperature for 160 minutes. The pH of the reaction mixture at 30 C. was found to be 7.8. The reaction mass was then cooled in an ice-bath for about 20 min. The cold suspension was filtered to remove insoluble material and the filtrate was concentrated under vacuo to dryness to provide 10.35 g (96.9%) of the title compound. IR (KBr) cm-1: 1790, 1740, 1690, 1600, 1520, 1495, 1350, 1240, 1180, 1080. 1 H-NMR (CDCl3): Delta 1.93 (s1 3H), 4.53 (s,2H), 5.05 (bs, 1H), 5.23 (m,2H), 5.33 (s,2H), 5.57 (d, 1H), J=4.5Hz), 6.18 (dd, 1H, J=4.5Hz), 6.9-8.1 (m, 9H, Ar).

Reference： [1]Patent: US5604222,1997,A

33
disodium hydrogenphosphate [ No CAS ]
[ 3481-09-2 ]
p-nitrobenzyl-6-phenoxy acetamido-2,2-dimethylpenam-3-carboxylate-1-oxide [ No CAS ]
4'-nitrobenzyl 7-phenoxyacetamido-3-methylenecepham-4-carboxylate sulfoxide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		EXAMPLE 12 p-nitrobenzyl-7-phenoxyacetamido-3-methylene cepham-4-carboxylate-1-oxide 15 g of disodium hydrogen orthophosphate were suspended in 300 ml 1,1,2 trichloroethane and subjected to azeotropic distillation. The contents were cooled and 10 g of p-nitrobenzyl-6-phenoxy acetamido-2, 2-dimethyl penam-3-carboxylate-1-oxide and 5.0 g of <strong>[3481-09-2]N-chlorophthalimide</strong> were added. The reaction proceeded as in Example 11. Yield of the title product was 7.5 g (75%).

Reference： [1]Patent: US5604222,1997,A

34
[ 3481-09-2 ]
p-nitrobenzyl-6-phenoxy acetamido-2,2-dimethylpenam-3-carboxylate-1-oxide [ No CAS ]
[ 78183-91-2 ]

Yield	Reaction Conditions	Operation in experiment
10.13 g (95%)	In toluene;	EXAMPLE 1 p-Nitrobenzyl 3-Methyl-2-(2-Chlorosulfinyl-4-Oxo-3-Phenoxyacetamido-1-Azetidinyl)-3-Butenoate 5 g of Dowex 1*16 (100-200 mesh), a Type I anion exchange resin (16% cross-linked with divinyl benzene (DVB)), was suspended in 300 ml of dry toluene. Moisture of the resin and of toluene was removed by azeotropic distillation using Dean-stark water trap. The mixture was cooled to 25 C. 10 g of p-nitrobenzyl-6-phenoxyacetamido-2,2-dimethylpenam-3-carboxylate-1-oxide and 5 g of <strong>[3481-09-2]N-chlorophthalimide</strong> were added. The reaction mixture was refluxed for 1/2 hours and then cooled to 10 C. The insoluble material was filtered and the filtrate was concentrated to dryness to provide 10.13 g (95%) of the title compound. IR (CHCl3): cm-1 1790, 1750, 1700, 1530, 1350, 1220, 1040. 1 H NMR (CDCl3): delta 1.90(s,3H), 4.53(s,2H), 5.13(m,3H), 5.3(s,2H), 5.55, (d,1H), 6.05(dd,1H) and 6.6-8.05(m,9H).

Reference： [1]Patent: US5070195,1991,A

35
[ 109-99-9 ]
[ 3481-09-2 ]
p-nitrobenzyl 6-phenoxyacetamidopenicillinate sulfoxide [ No CAS ]
azetidinone-4-sulfinic acid sodium salt [ No CAS ]
azetidin-2-one-4-sulfinic acid [ No CAS ]
[ 78109-48-5 ]

Yield	Reaction Conditions	Operation in experiment
50%	With hydrogenchloride; In water; ethyl acetate; acetone; toluene;	EXAMPLE 1 p-Nitrobenzyl 3-methyl-2-(2-oxo-4-sulfino-3-phenoxyacetamido-1-azetidinyl)-3-butenoate A solution of 100 g. of p-nitrobenzyl 6-phenoxyacetamidopenicillinate sulfoxide in 3500 ml. of toluene containing in suspension 44 g. of calcium oxide was heated to the reflux temperature in a five-liter flask equipped with a stirrer, thermometer and a Dean-Stark trap. The mixture was refluxed until 100 ml. of toluene were collected in the trap. The heat was removed and 44 g. of <strong>[3481-09-2]N-chlorophthalimide</strong> and 30 ml. of butylene oxide were added. The reaction mixture was then heated at the reflux temperature for about one hour and forty minutes. The butylene oxide was distilled off with toluene and collected in the trap and the reaction mixture was then cooled to about 0 C. in an ice bath. The 4-chlorosulfinylazetidinone product was hydrolyzed in solution by adding one liter of 1 N hydrochloric acid with vigorous stirring of the two-phase mixture. After one hour of stirring, 300 ml. of acetone was added and the organic phase was washed three times with 500 ml-portions of brine. To the organic phase were added 400 ml. of distilled water and the pH was adjusted to 8 with sodium bicarbonate. The aqueous phase containing the azetidinone-4-sulfinic acid sodium salt was washed with ethyl acetate and then layered with 800 ml. of fresh ethyl acetate. The pH was adjusted to 2 with 1 N hydrochloric acid. The organic phase was separated, dried over magnesium sulfate and evaporated to dryness on a rotary evaporator. The azetidinone-4-sulfinic acid was obtained as a white foam in 50% yield. NMR (CDCl3): signals delta at 1.9 (s, 3H, CH3), 4.46 (s, 2H, side chain CH2), 4.88 (d, 1H, J=5.0 Hz, azet. H), 5.0 (s, 1H, CHCOOpNB), 5.2 (m, 2H, C2 =), 5.3 (s, 2H, CH2 ester), 5.8 (dd, 1H, J=5.0 and 8.0 Hz), 16.-8.4 (m, 9H, aromatic H) and 8.4 (d, 1H, J=8.0 Hz NH).

Reference： [1]Patent: US4368156,1983,A

36
[ 3481-09-2 ]
2-chlorosulfinyl-azetidin-4-one [ No CAS ]
diphenylmethyl 6-phenoxyacetamidopenicillanate sulfoxide [ No CAS ]
diphenylmethyl 3-methyl-2-(2-oxo-4-chloro-3-phenoxyacetamido-1-azetidinyl)-3-butenoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With N-chloro-succinimide; sodium hydrogencarbonate; In diethyl ether; toluene;	EXAMPLE 6 Diphenylmethyl 3-methyl-2-(2-oxo-4-chloro-3-phenoxyacetamido-1-azetidinyl)-3-butenoate A suspension of 12.5 g. of poly-(4-vinylpyridine) divinylbenzene crosslinked copolymer (2% crosslinked) in one liter of toluene was heated at the reflux temperature while 150 ml. of toluene were distilled off with water. Heating was discontinued and 21.2 g. (40 mmole) of diphenylmethyl 6-phenoxyacetamidopenicillanate sulfoxide and 7.98 g. (44 mmole) of <strong>[3481-09-2]N-chlorophthalimide</strong> were added to the warm suspension. The reaction mixture was reheated at the reflux temperature for 100 min. after which the mixture was cooled to 10 C. and was stirred for 10 min. The insoluble copolymer and phthalimide were filtered and discarded. To the filtrate containing the azetidinone-4-sulfinyl chloride were added 10.72 g. (80 mmole) of N-chlorosuccinimide and 200 ml. of a saturated aqueous solution of sodium bicarbonate and the mixture vigorously stirred for one hour. The organic phase was separated, washed 3 times with brine, dried over magnesium sulfate, and evaporated to dryness under reduced pressure. The reaction product obtained as a gum was dissolved in 50 ml. of diethyl ether. After standing for 15 min. at room temperature and after scratching the flask to induce crystallization the product crystallized from solution. The product was filtered and washed three times with diethyl ether. There were obtained 10.1 g. of the title compound.

Reference： [1]Patent: US4368156,1983,A

37
[ 1074-82-4 ]
[ 3481-09-2 ]
potassium chloride [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
46.4 grams (95.% yield)	With chlorine; In dichloromethane; water;	EXAMPLE 5 Chlorine gas was added to one liter of methylene chloride for 20 minutes at 0 C. during which time saturation was achieved. Potassium phthalimide (50 grams; 270 mmoles) was added to the chlorine-saturated methylene chloride. Cooling was discontinued, and the mixture was stirred for two hours during which time the mixture warmed to 20 C. The resulting slightly greenish-yellow mixture was evaporated to a slush without filtering, and water was added to the mixture to dissolve the resulting potassium chloride. The total mixture was filtered, and the solid which was collected was washed with water and then with heptane. The solid was vacuum-dried overnight to obtain 46.4 grams (95.% yield) of N-chlorophthalimide.

Reference： [1]Patent: US4082766,1978,A

38
[ 33081-78-6 ]
[ 3481-09-2 ]

Yield	Reaction Conditions	Operation in experiment
90%	In dichloromethane;	EXAMPLE 3 To 170 ml. of methylene chloride saturated with chlorine and maintained at 0 C. were added 8.3 grams (49 mmoles) of sodium phthalimide. The resulting mixture was warmed to 20 C. and was stirred for 1.5 hours. The resulting precipitated sodium chloride was removed by filtration, and the filtrate was evaporated to dryness to afford 8.0 grams (90% yield) of N-chlorophthalimide.

Reference： [1]Patent: US4082766,1978,A

39
[ 3481-09-2 ]
p-nitrobenzyl-6-phenyl acetamido-2,2-dimethyl penam-3-carboxylate-1-oxide [ No CAS ]
[ 136918-14-4 ]

Yield	Reaction Conditions	Operation in experiment
	With methyloxirane; In toluene;	A. Reaction in the absence of calcium oxide. Toluene (2.1 liters) was dried by distillative removal of about 160 ml. of the solvent. An additional 50 ml. of toluene were removed for use in transferring the reactants to the reaction medium. Heating was discontinued, and 17.1 grams (34 mmoles) of p-nitrobenzyl 6-phenylacetamido-2,2-dimethylpenam-3-carboxylate-1-oxide, 7.8 grams (37.4 mmoles) of <strong>[3481-09-2]N-chlorophthalimide</strong>, and 12 ml. of propylene oxide were added. The mixture was refluxed at 103 C. for 100 minutes after which distillative removal was begun. A total of 170 ml. of material was removed over about 30 minutes. The resulting mixture was cooled to 0-5 C. The resulting crystalline phthalimide by-product then was removed by filtration. The filtrate was added to a precooled mixture of 8.5 ml. of stannic chloride in toluene. The mixture was stirred overnight during which time it was permitted to warm to room temperature. The resulting solid was collected by filtration and washed thoroughly with toluene. The solid then was dissolved in a mixture of 85 ml. of acetone and 170 ml. of ethyl acetate. The solution then was extracted twice with 170 ml. of water. The organic layer was separated, evaporated to about one-half volume, cooled to room temperature during which time crystallization occurred. The title compound (4.0 grams; 25%) was recovered by filtration.

Reference： [1]Patent: US4075203,1978,A

40
[ 136918-14-4 ]
4-vinylpyridine-divinylbenzene [ No CAS ]
[ 3481-09-2 ]

Yield	Reaction Conditions	Operation in experiment
	With chlorine; In quinoline; dichloromethane;	EXAMPLE 2 N-Chlorophthalimide (Method A) To 2.45 g. of 4-vinylpyridine-divinylbenzene copolymer (7.38 mcg./g., 10% excess) in 200 ml. of methylene chloride was introduced chlorine until the solvent turned slightly greenish yellow. Phthalimide (7.35 g, 50 mM) was added in one portion. Quinoline (three drops) was added, and the reaction mixture was stirred at room temperature for five hours. The reaction mixture was filtered to remove reacted and unreacted polymer. The polymer was washed twice with methylene chloride (15 ml.). The original filtrate and the washing were combined and evaporated slowly to about one-third volume. White crystals formed at this step, but the mixture was kept in a refrigerator overnight to complete the crystallization. The crystals were collected by filtration. After drying under vacuum, there was obtained 8.70 g. (95.9% yield) of the title product, m.p. 179.5-180 C., identified by infrared spectral analysis. Percent chlorine: Found 17.6; calculated 19.5%.

Reference： [1]Patent: US4212977,1980,A

41
[ 3481-09-2 ]
[ 603-36-1 ]
(C₆H₅)3Sb(Cl)N(CO)2C₆H₄ [ No CAS ]

Reference： [1]Patent: DD83136,1971,
C.A.,1973,vol. 78,p. 43715
[2]Gmelin Handbuch der Anorganischen Chemie,Gmelin Handbook: Sb: Org.Comp.1, 1.1.1.1.6.4.5, page 78 - 82

42
[ 3481-09-2 ]
[ 593-91-9 ]
(CH₃)3BiC₈H₄O₂N⁽¹⁺⁾*Cl^(1-) [ No CAS ]

Reference： [1]Gmelin Handbuch der Anorganischen Chemie,Gmelin Handbook: Bi: Org.Verb., 3.2.3.1, page 154 - 155
[2]Patent: DE83136,1971,
C. A.,1973,vol. 78,p. 43715

43
[ 3481-09-2 ]
[ 603-33-8 ]
(C₆H₅)3BiC₈H₄O₂N⁽¹⁺⁾*Cl^(1-) [ No CAS ]

Reference： [1]Gmelin Handbuch der Anorganischen Chemie,Gmelin Handbook: Bi: Org.Verb., 3.2.3.1, page 154 - 155
[2]Patent: DE83136,1971,
C. A.,1973,vol. 78,p. 43715

44
[ 3481-09-2 ]
[(1-pyrrolylimido)F(dpe)2tungsten](BF₄) [ No CAS ]
W(((C₆H₅)2PCH₂)2)2FNN(CH)3(CCl)⁽¹⁺⁾*BF₄^(1-)=[W(((C₆H₅)2PCH₂)2)2FNN(CH)3(CCl)]BF₄ [ No CAS ]
W(((C₆H₅)2PCH₂)2)2FNN(CH)2(CCl)2⁽¹⁺⁾*BF₄^(1-)*0.5CH₂Cl₂=[W(((C₆H₅)2PCH₂)2)2FNN(CH)2(CCl)2]BF₄*0.5CH₂Cl₂ [ No CAS ]

Reference： [1]Journal of the American Chemical Society,1995,vol. 117,p. 12181 - 12193

45
[ 3481-09-2 ]
trichlorogermane etherate [ No CAS ]
[ 95601-29-9 ]

Reference： [1]Journal of general chemistry of the USSR,1984,vol. 54,p. 2314 - 2317
J.Gen.Chem.USSR (Engl.Transl.),1984,vol. 54,p. 2590 - 2593

46
[ 3481-09-2 ]
[ 27309-70-2 ]
tri(α-naphthyl)antimony(V) ((NCO(C6H4)C)O)(Cl) [ No CAS ]

Reference： [1]Synthesis and Reactivity in Inorganic and Metal-Organic Chemistry,2002,vol. 32,p. 399 - 417

47
[ 3481-09-2 ]
[ 155155-73-0 ]
[ 590-86-3 ]
[ 1388217-32-0 ]