1-Chloro-4-isocyanato-2-(trifluoromethyl) benzene → HCID 24997653, compound

HRID 659002Notes

Reaction equation

HRID 659002 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)=[CH:18][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:17]=[CH:18][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)=[CH:32][CH:33]=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 67524085HCID 67524085, compound

Product 1

HCID 24997653HCID 24997653, compoundYield 46.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 494 mg (2.23 mmol) 4-chloro-3-trifluoromethyl-phenyl isocyanate in 10 ml THF was added within 15 min. to a solution of 580 mg (2.23 mmol) 3-[4-(4-Amino-phenoxy)-pyrimidin-2-ylamino]-propan-1-ol in 10 ml THF and stirring continued overnight. The reaction mixture was evaporated and purified by HPLC/MS (Reprosil 100 C18, 10 μm, methanol/water 80:20) to give 500 mg oil that solidified by treatment with a small amount of ether. The precipitate was filtered and dried to yield 400 mg of the title compound.

Workup

  1. customThe reaction mixture was evaporated
  2. custompurified by HPLC/MS (Reprosil 100 C18, 10 μm, methanol/water 80:20)

Sources & evidence

ORD record
ord-1336ed592f1f4e94a480830686643f8b
Source dataset
uspto-grants-2011_12
Patent number
US08080552B2

Reaction notes

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