1-Chloro-4-isocyanato-2-(trifluoromethyl) benzene → HCID 67524051, compound

HRID 659004Notes

Reaction equation

HRID 659004 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].[CH3:15][S:16][C:17]1[N:22]=[C:21]([O:23][C:24]2[CH:29]=[CH:28][C:27]([NH2:30])=[CH:26][CH:25]=2)[CH:20]=[CH:19][N:18]=1>C1COCC1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]([NH:30][C:27]2[CH:26]=[CH:25][C:24]([O:23][C:21]3[CH:20]=[CH:19][N:18]=[C:17]([S:16][CH3:15])[N:22]=3)=[CH:29][CH:28]=2)=[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 67523926HCID 67523926, compound

Product 1

HCID 67524051HCID 67524051, compoundYield 86.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 4.81 g (21.7 mmol) 4-chloro-3-trifluoromethyl-phenyl isocyanate in 100 ml THF was added within 45 min. drop by drop at 0° C. to a solution of 5.06 g (21.7 mmol) 4-(2-methylsulfanyl-pyrimidin-4-yloxy)-phenylamine and stirring continued at r.t. overnight. The reaction mixture was evaporated and leached with 100 ml dichloromethane. The precipitate was isolated and dried to give 8.53 g (86%) 1-(4-Chloro-3-trifluoromethyl-phenyl)-3-[4-(2-methylsulfanyl-pyrimidin-4-yloxy)-phenyl]-urea.

Workup

  1. customThe reaction mixture was evaporated
  2. customThe precipitate was isolated
  3. customdried

Sources & evidence

ORD record
ord-b078bb5e6b1b4807a87fb62f18bc18f6
Source dataset
uspto-grants-2011_12
Patent number
US08080552B2

Reaction notes

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