2-Chlorobenzoyl isocyanate → HCID 13229715, compound

HRID 615201Notes

Reaction equation

HRID 615201 reaction equation
[Cl:1][C:2]1[CH:12]=[CH:11][CH:10]=[CH:9][C:3]=1[C:4]([N:6]=[C:7]=[O:8])=[O:5].[F:13][C:14]([F:34])([F:33])[O:15][C:16]1[CH:21]=[CH:20][C:19]([NH:22][S:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=2[N+:30]([O-:32])=[O:31])=[CH:18][CH:17]=1>C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:12]=[CH:11][CH:10]=[CH:9][C:3]=1[C:4]([NH:6][C:7]([N:22]([C:19]1[CH:20]=[CH:21][C:16]([O:15][C:14]([F:13])([F:33])[F:34])=[CH:17][CH:18]=1)[S:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=1[N+:30]([O-:32])=[O:31])=[O:8])=[O:5]

Participants

4

Reactant 2

HCID 99423112-Chlorobenzoyl isocyanateHCID 13229714N-[(2-Nitrophenyl)sulfanyl]-4-(trifluoromethoxy)aniline

Product 1

HCID 13229715HCID 13229715, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
-5 °C

Procedure

A solution of 50 g of 2-chlorobenzoyl isocyanate in 50 ml of dry toluene was added to a stirred solution of 60 g of N-[4-(trifluoromethoxy)phenyl]-2-nitrobenzenesulphenamide in 100 ml of the same solvent. The reaction was slightly exothermic, reaching a maximum temperature of 35° C. After 4 days at room temperature, the reaction mixture was cooled to -5° C. and the crystalline cake of product was broken up under cold toluene, filtered, washed with toluene followed by cold light petroleum (b.p. 40°-60° C.) and dried at 40° C. under reduced pressure, to give 1, as pale yellow crystals, m.p. 155°-158° C. (with decomposition).

Workup

  1. customa maximum temperature of 35° C
  2. filtrationfiltered
  3. washwashed with toluene
  4. customdried at 40° C. under reduced pressure
  5. customto give 1

Sources & evidence

ORD record
ord-ca3a84581a9447479611c333513066dc
Source dataset
uspto-grants-1985_02
Patent number
US04497822

Reaction notes

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