3-(Trifluoromethyl)phenyl isocyanate → 1-[4-(6-Methylsulfanyl-pyrimidin-4-yloxy)-phenyl]-3-(3-trifluoromethyl-phenyl)-urea

HRID 659028Notes

Reaction equation

HRID 659028 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.[F:17][C:18]([F:29])([F:28])[C:19]1[CH:20]=[C:21]([N:25]=[C:26]=[O:27])[CH:22]=[CH:23][CH:24]=1>C1COCC1>[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]([NH:16][C:26]([NH:25][C:21]3[CH:22]=[CH:23][CH:24]=[C:19]([C:18]([F:17])([F:28])[F:29])[CH:20]=3)=[O:27])=[CH:12][CH:11]=2)[CH:4]=1

Participants

4

Reactant 2

HCID 94833-(Trifluoromethyl)phenyl isocyanateHCID 675239014-(6-Methylsulfanyl-pyrimidin-4-yloxy)-phenylamine

Product 1

HCID 675239161-[4-(6-Methylsulfanyl-pyrimidin-4-yloxy)-phenyl]-3-(3-trifluoromethyl-phenyl)-ureaYield 76.1%

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 3-(trifluoromethyl)phenyl isocyanate (790 μl, 5.5 mmol) in THF (24 ml) is added 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 1.76 g (75%) of a white powder.

Workup

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

Sources & evidence

ORD record
ord-989e36c012ac4987971902c61af8de1c
Source dataset
uspto-grants-2011_12
Patent number
US08080552B2

Reaction notes

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