1-Chloro-4-isocyanato-2-(trifluoromethyl) benzene → HCID 67523907, compound

HRID 659021Notes

Reaction equation

HRID 659021 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]=[C:9]=[O:10])=[CH:4][C:3]=1[C:11]([F:14])([F:13])[F:12].[F:15][C:16]1[CH:21]=[C:20]([O:22][C:23]2[CH:28]=[CH:27][N:26]=[C:25]([S:29][CH3:30])[N:24]=2)[CH:19]=[CH:18][C:17]=1[NH2:31]>C1COCC1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]([NH:31][C:17]2[CH:18]=[CH:19][C:20]([O:22][C:23]3[CH:28]=[CH:27][N:26]=[C:25]([S:29][CH3:30])[N:24]=3)=[CH:21][C:16]=2[F:15])=[O:10])=[CH:4][C:3]=1[C:11]([F:12])([F:13])[F:14]

Participants

4

Reactant 2

HCID 27332651-Chloro-4-isocyanato-2-(trifluoromethyl) benzeneHCID 67523950HCID 67523950, compound

Product 1

HCID 67523907HCID 67523907, compoundYield 40.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 162 mg (0.732 mmol) 4-chloro-3-trifluoromethyl-phenyl isocyanate in 3 ml THF was added within 5 min. drop by drop at 0° C. to a solution of 184 mg (0.732 mmol) 2-fluoro-4-(2-methylsulfanyl-pyrimidin-4-yloxy)-phenylamine and stirring continued at r.t. overnight. The reaction mixture was evaporated and treated with 10 ml ether. Isolation of the precipitate gave 140 mg (40%) 1-(4-chloro-3-trifluoromethyl-phenyl)-3-[2-fluoro-4-(2-methylsulfanyl-pyrimidin-4-yloxy)-phenyl]-urea.

Workup

  1. customThe reaction mixture was evaporated
  2. additiontreated with 10 ml ether

Sources & evidence

ORD record
ord-3730313cc54249e9988885c51e607361
Source dataset
uspto-grants-2011_12
Patent number
US08080552B2

Reaction notes

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