1-Chloro-4-isocyanato-2-(trifluoromethyl) benzene → HCID 24997345, compound

HRID 659011Notes

Reaction equation

HRID 659011 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].[NH2:15][C:16]1[CH:33]=[CH:32][C:19]([O:20][C:21]2[CH:26]=[CH:25][N:24]=[C:23]([NH:27][CH2:28][CH2:29][CH2:30][OH:31])[N:22]=2)=[C:18]([Cl:34])[CH:17]=1>C1COCC1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]([NH:15][C:16]2[CH:33]=[CH:32][C:19]([O:20][C:21]3[CH:26]=[CH:25][N:24]=[C:23]([NH:27][CH2:28][CH2:29][CH2:30][OH:31])[N:22]=3)=[C:18]([Cl:34])[CH:17]=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 67523919HCID 67523919, compound

Product 1

HCID 24997345HCID 24997345, compoundYield 27.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 205 mg (0.926 mmol) 4-chloro-3-trifluoromethyl-phenyl isocyanate in 3 ml THF was added within 10 min. to a solution of 273 mg (0.926 mmol) 3-[4-(4-amino-2-chloro-phenoxy)-pyrimidin-2-ylamino]-propan-1-ol in 3 ml THF and stirring continued overnight. The reaction mixture was evaporated and purified by chromatography on silica (dichloromethane/ethanol 97:3). The obtained material was stirred with dichloromethane. The precipitate was filtered and dried to yield 130 mg of the title compound.

Workup

  1. customThe reaction mixture was evaporated
  2. custompurified by chromatography on silica (dichloromethane/ethanol 97:3)
  3. stirringThe obtained material was stirred with dichloromethane
  4. filtrationThe precipitate was filtered
  5. customdried

Sources & evidence

ORD record
ord-bb6fee793099445b90aa6b7fbb89c3f0
Source dataset
uspto-grants-2011_12
Patent number
US08080552B2

Reaction notes

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