2,6-Difluorobenzoyl isocyanate → HCID 19873185, compound

HRID 466216Notes

Reaction equation

HRID 466216 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:32]=[C:31]([C:33]([F:36])([F:35])[F:34])[CH:30]=[CH:29][C:16]=1[O:17][C:18]1[CH:23]=[CH:22][C:21]([NH:24][C:25]([NH2:27])=[O:26])=[C:20]([F:28])[CH:19]=1>C1(C)C=CC=CC=1>[Cl:14][C:15]1[CH:32]=[C:31]([C:33]([F:34])([F:36])[F:35])[CH:30]=[CH:29][C:16]=1[O:17][C:18]1[CH:23]=[CH:22][C:21]([NH:24][C:25]([NH:27][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])=[O:26])=[C:20]([F:28])[CH:19]=1

Participants

4

Reactant 2

HCID 27333692,6-Difluorobenzoyl isocyanateHCID 19873174N-[4-(2-Chloro-4-trifluoromethylphenoxy)-2-fluorophenyl] urea

Product 1

HCID 19873185HCID 19873185, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
20 °C

Procedure

2,6-Difluorobenzoyl isocyanate (1.8 g) was added to a solution of N-(4-(2-chloro-4-(trifluoromethyl)phenoxy)-2-fluorophenyl)urea (3.2 g) in dry toluene (50 ml), and the resulting solution was stirred at ambient temperature (20° C.) for 48 hours. The product was then filtered from the reaction mixture, washed with a small amount of 1:2 v/v diethyl ether/light petroleum ether, and dried to yield N-(((((4-(2-chloro-4-(trifluoromethyl)phenoxy)-2-fluorophenyl)-amino)carbonyl)amino)carbonyl)-2,6-difluorobenzamide as a colourless crystalline solid (4.3 g, 90%), mp 190-192° C.

Workup

  1. filtrationThe product was then filtered from the reaction mixture
  2. washwashed with a small amount of 1:2 v/v diethyl ether/light petroleum ether
  3. customdried

Sources & evidence

ORD record
ord-0715bab3acc841abb0b112dd49c16262
Source dataset
uspto-grants-1992_10
Patent number
US05155135

Reaction notes

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