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

HRID 2351540Notes

Reaction equation

HRID 2351540 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:36]=[C:35]([C:37]([F:40])([F:39])[F:38])[CH:34]=[CH:33][C:16]=1[O:17][C:18]1[CH:23]=[CH:22][C:21]([NH:24][S:25][N:26]2[CH2:31][CH2:30][O:29][CH2:28][CH2:27]2)=[C:20]([F:32])[CH:19]=1>C1(C)C=CC=CC=1>[Cl:14][C:15]1[CH:36]=[C:35]([C:37]([F:40])([F:39])[F:38])[CH:34]=[CH:33][C:16]=1[O:17][C:18]1[CH:23]=[CH:22][C:21]([N:24]([S:25][N:26]2[CH2:31][CH2:30][O:29][CH2:28][CH2:27]2)[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])=[C:20]([F:32])[CH:19]=1

Participants

4

Reactant 2

HCID 27333692,6-Difluorobenzoyl isocyanateHCID 15085830[4-[2-Chloro-4-(trifluoromethyl)phenoxy]-2-fluorophenyl][(4-morpholinyl)thio]amine

Product 1

HCID 15085831N-[[[4-[2-chloro-4-(trifluoromethyl)phenoxy]-2-fluorophenyl][(4-morpholinyl)thio]amino]carbonyl]-2,6-difluorobenzamideYield 58.2%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

2,6-Difluorobenzoyl isocyanate (1.4 g) in a 1:1 (v/v) mixture of toluene and petroleum ether (10 ml) was added to a solution of the compound produced by Example 6 (3 g) in the same solvent (15 ml), at ambient temperature. The solution was stirred for two hours and placed in a freezer overnight (-5° to 0° C.). The solvent was removed by evaporation, and the residue was chromatographed twice on silica, firstly using dichloromethane as eluant and secondly using a 1:1 (v/v) mixture of diethyl ether and petroleum ether, to yield the title compound (2.5 g), m.p. 77°-80° C.

Workup

  1. waitplaced in a freezer overnight
  2. custom(-5° to 0° C.)
  3. customThe solvent was removed by evaporation
  4. customthe residue was chromatographed twice on silica, firstly using dichloromethane as eluant
  5. additiona 1:1 (v/v) mixture of diethyl ether and petroleum ether

Sources & evidence

ORD record
ord-e9749931db0e41bd93a12b737f4bde41
Source dataset
uspto-grants-1989_10
Patent number
US04873327

Reaction notes

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