1-Chloro-4-isocyanato-2-(trifluoromethyl) benzene → 1-(4-Chloro-3-trifluoromethyl-phenyl)-3-[4-(6-methylsulfanyl-pyrimidin-4-yloxy)-phenyl]-urea

HRID 659030Notes

Reaction equation

HRID 659030 reaction equation
[CH3:1][S:2][C:3]1[N:8]=[CH:7][N:6]=[C:5]([O:9][C:10]2[CH:15]=[CH:14][C:13]([NH2:16])=[CH:12][CH:11]=2)[CH:4]=1.[Cl:17][C:18]1[CH:23]=[CH:22][C:21]([N:24]=[C:25]=[O:26])=[CH:20][C:19]=1[C:27]([F:30])([F:29])[F:28]>C1COCC1>[Cl:17][C:18]1[CH:23]=[CH:22][C:21]([NH:24][C:25]([NH:16][C:13]2[CH:14]=[CH:15][C:10]([O:9][C:5]3[CH:4]=[C:3]([S:2][CH3:1])[N:8]=[CH:7][N:6]=3)=[CH:11][CH:12]=2)=[O:26])=[CH:20][C:19]=1[C:27]([F:28])([F:29])[F:30]

Participants

4

Reactant 2

HCID 27332651-Chloro-4-isocyanato-2-(trifluoromethyl) benzeneHCID 675239014-(6-Methylsulfanyl-pyrimidin-4-yloxy)-phenylamine

Product 1

HCID 675241261-(4-Chloro-3-trifluoromethyl-phenyl)-3-[4-(6-methylsulfanyl-pyrimidin-4-yloxy)-phenyl]-ureaYield 71.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 4-(6-methylsulfanyl-pyrimidin-4-yloxy)-phenylamine (1.3 g, 5.5 mmol) in THF (24 ml) is cooled to 0° C. A solution of 4-chloro-3-(trifluoromethyl)phenyl isocyanate (1.22 g, 5.5 mmol) in THF (24 ml) is added dropwise and stirring is continued overnight at r.t. The solvent is evaporated and the crude product is purified by silica gel chromatography using an ethyl acetate/heptane eluent (1:1) to give 1.78 g (70%) of a white solid.

Workup

  1. customThe solvent is evaporated
  2. customthe crude product is purified by silica gel chromatography

Sources & evidence

ORD record
ord-f423b4486d524a4897165fe6ab5c35cf
Source dataset
uspto-grants-2011_12
Patent number
US08080552B2

Reaction notes

Loading…