2,6-Difluorobenzoyl isocyanate → HCID 20397098, compound

HRID 462700Notes

Reaction equation

HRID 462700 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].[F:14][C:15]([F:38])([F:37])[C:16]1[CH:21]=[CH:20][C:19]([NH:22][S:23][C:24]2[CH:36]=[CH:35][CH:34]=[CH:33][C:25]=2[C:26]([O:28][CH2:29][CH2:30][CH2:31][CH3:32])=[O:27])=[CH:18][CH:17]=1>C1(C)C=CC=CC=1>[F:1][C:2]1[CH:12]=[CH:11][CH:10]=[C:9]([F:13])[C:3]=1[C:4]([NH:6][C:7]([N:22]([C:19]1[CH:18]=[CH:17][C:16]([C:15]([F:14])([F:37])[F:38])=[CH:21][CH:20]=1)[S:23][C:24]1[CH:36]=[CH:35][CH:34]=[CH:33][C:25]=1[C:26]([O:28][CH2:29][CH2:30][CH2:31][CH3:32])=[O:27])=[O:8])=[O:5]

Participants

4

Reactant 2

HCID 27333692,6-Difluorobenzoyl isocyanateHCID 20397100HCID 20397100, compound

Product 1

HCID 20397098HCID 20397098, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 2,6-difluorobenzoyl isocyanate (1.1 g) in dry toluene (5.0 ml) was added to a stirred solution of butyl 2-[[[4-(trifluoromethyl)phenyl]amino]thio]benzoate (1.9 g) in the same solvent (7.0 ml) at room temperature. After 18 hours, the reaction mixture was cooled to -5°, and the crystalline precipitate was separated, washing with cold toluene followed by light petroleum. The pure product was obtained as colourless crystals (2.5 g, melting point 79°-81°) after recrystallisation from diethyl ether/light petroleum.

Workup

  1. temperaturethe reaction mixture was cooled to -5°
  2. customthe crystalline precipitate was separated
  3. washwashing with cold toluene

Sources & evidence

ORD record
ord-0a564fec40b34358b187564a2b2ce4fc
Source dataset
uspto-grants-1985_05
Patent number
US04517193

Reaction notes

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