2,6-Difluorobenzoyl isocyanate → N-[[[4-[2-chloro-4-(trifluoromethyl)phenoxy]-2-fluorophenyl][[(2,6-difluorobenzoyl)amino]carbonyl]amino]thio]-N-methylbutanamide

HRID 1731789Notes

Reaction equation

HRID 1731789 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:37]=[C:36]([C:38]([F:41])([F:40])[F:39])[CH:35]=[CH:34][C:16]=1[O:17][C:18]1[CH:23]=[CH:22][C:21]([NH:24][S:25][N:26]([CH3:32])[C:27](=[O:31])[CH2:28][CH2:29][CH3:30])=[C:20]([F:33])[CH:19]=1>C1(C)C=CC=CC=1>[Cl:14][C:15]1[CH:37]=[C:36]([C:38]([F:39])([F:40])[F:41])[CH:35]=[CH:34][C:16]=1[O:17][C:18]1[CH:23]=[CH:22][C:21]([N:24]([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:25][N:26]([CH3:32])[C:27](=[O:31])[CH2:28][CH2:29][CH3:30])=[C:20]([F:33])[CH:19]=1

Participants

4

Reactant 2

HCID 27333692,6-Difluorobenzoyl isocyanateHCID 20183877N-[[[4-[2-chloro-4-(trifluoromethyl)phenoxy]-2-fluorophenyl]amino]thio]-N-methylbutanamide

Product 1

HCID 20183879N-[[[4-[2-chloro-4-(trifluoromethyl)phenoxy]-2-fluorophenyl][[(2,6-difluorobenzoyl)amino]carbonyl]amino]thio]-N-methylbutanamide

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 2.0 g of 2,6-difluorobenzoylisocyanate in 5 ml of a 1:1 v:v mixture of toluene and petroleum ether was added at room temperature over 30 minutes to a stirred solution of 4.4 g of 33 in 20 ml of the same solvent. After stirring at room temperature for 2 hours, the mixture was filtered, and the collected solid product was recrystallized from a mixture of diethyl ether and petroleum ether to give 36, as a white solid, m.p.: 136°-138° C.

Workup

  1. filtrationthe mixture was filtered
  2. customthe collected solid product was recrystallized from a mixture of diethyl ether and petroleum ether

Sources & evidence

ORD record
ord-31365137c2804990b88e294258166630
Source dataset
uspto-grants-1986_11
Patent number
US04623658

Reaction notes

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