2,6-Difluorobenzoyl isocyanate → HCID 13229719, compound

HRID 615204Notes

Reaction equation

HRID 615204 reaction equation
[F:1][C:2]1[CH:12]=[CH:11][CH:10]=[C:9]([F:13])[C:3]=1[C:4]([N:6]=[C:7]=[O:8])=[O:5].[Cl:14][C:15]1[CH:20]=[CH:19][C:18]([NH:21][S:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=2[N+:29]([O-:31])=[O:30])=[CH:17][CH:16]=1>C1(C)C=CC=CC=1.C(N(CC)CC)C>[Cl:14][C:15]1[CH:16]=[CH:17][C:18]([N:21]([C:7]([NH:6][C:4](=[O:5])[C:3]2[C:2]([F:1])=[CH:12][CH:11]=[CH:10][C:9]=2[F:13])=[O:8])[S:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=2[N+:29]([O-:31])=[O:30])=[CH:19][CH:20]=1

Participants

5

Reactant 2

HCID 27333692,6-Difluorobenzoyl isocyanateHCID 124821594-Chloro-N-[(2-nitrophenyl)sulfanyl]aniline

Product 1

HCID 13229719HCID 13229719, compound

Reagents, catalysts & solvents 2

HCID 8471TriethylamineCatalystHCID 1140TolueneSolvent

Conditions

Temperature
-5 °C

Procedure

A solution of 1.8 g of 2,6-difluorobenzoyl isocyanate in 15 ml of dry toluene was added over 15 minutes to a stirred solution of 2.8 g of N-(4-chlorophenyl)-2-nitrobenzenesulphenamide in 35 ml of the same solvent at room temperature. After stirring overnight, the reaction was incomplete. A few drops of triethylamine were added, and after a further 24 hours, the reaction mixture was cooled to -5° C. and filtered, and the pale yellow product was washed with cold toluene. Traces of toluene were removed by drying under reduced pressure at about 40° C. for 3 days, to give 5, as a solid, m.p.: 176°-178° C.

Workup

  1. waitafter a further 24 hours
  2. filtrationfiltered
  3. washthe pale yellow product was washed with cold toluene
  4. customTraces of toluene were removed
  5. customby drying under reduced pressure at about 40° C. for 3 days
  6. customto give 5

Sources & evidence

ORD record
ord-c23f4dddd0a740869b1d72001ac84b6d
Source dataset
uspto-grants-1985_02
Patent number
US04497822

Reaction notes

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