2-Chlorobenzoyl isocyanate → HCID 13229718, compound

HRID 615203Notes

Reaction equation

HRID 615203 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:32])([F:31])[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[CH3:30])=[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:31])[F:32])=[CH:17][CH:18]=1)[S:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=1[CH3:30])=[O:8])=[O:5]

Participants

4

Reactant 2

HCID 99423112-Chlorobenzoyl isocyanateHCID 20429527N-[(2-Methylphenyl)sulfanyl]-4-(trifluoromethoxy)aniline

Product 1

HCID 13229718HCID 13229718, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
-5 °C

Procedure

A solution of 2.0 g of 2-chlorobenzoyl isocyanate in 5 ml of dry toluene was added to a stirred suspension of 3.0 g of N-[4-(trifluoromethoxy)phenyl]-2-methyl-benzenesulphenamide in 40 ml of dry light petroleum at room temperature. After a few minutes, the reaction mixture became clear and subsequently the product came out of solution as an oil which eventually crystallized. After 24 hours the reaction mixture was cooled to -5° C. and filtered, and the pale purple product was washed with cold light petroluem. Recrystallization from ether/light petroleum gave 4, as colorless crystals, m.p.: 79°-80° C.

Workup

  1. waitAfter a few minutes
  2. customeventually crystallized
  3. filtrationfiltered
  4. washthe pale purple product was washed with cold light petroluem
  5. customRecrystallization from ether/light petroleum
  6. customgave 4

Sources & evidence

ORD record
ord-ed202e8dc4ad469fa1373a3df1e789ab
Source dataset
uspto-grants-1985_02
Patent number
US04497822

Reaction notes

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