2-(Trifluoromethyl)benzoyl chloride → HCID 21890190, compound

HRID 721932Notes

Reaction equation

HRID 721932 reaction equation
FC(F)(F)C1C=CC=CC=1C(Cl)=O.[CH3:14][O:15][C:16]1[CH:17]=[C:18]2[C:23](=[CH:24][C:25]=1[O:26][CH3:27])[N:22]=[CH:21][N:20]=[C:19]2[O:28][C:29]1[CH:35]=[CH:34][C:32]([NH2:33])=[CH:31][CH:30]=1.[F:36][C:37]([F:50])([F:49])[C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][C:39]=1[C:44]([N:46]=[C:47]=[S:48])=[O:45]>C1(C)C=CC=CC=1.C(O)C>[F:49][C:37]([F:36])([F:50])[C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][C:39]=1[C:44]([N:46]=[C:47]=[S:48])=[O:45].[CH3:14][O:15][C:16]1[CH:17]=[C:18]2[C:23](=[CH:24][C:25]=1[O:26][CH3:27])[N:22]=[CH:21][N:20]=[C:19]2[O:28][C:29]1[CH:35]=[CH:34][C:32]([NH:33][C:47]([NH:46][C:44](=[O:45])[C:39]2[CH:40]=[CH:41][CH:42]=[CH:43][C:38]=2[C:37]([F:36])([F:50])[F:49])=[S:48])=[CH:31][CH:30]=1

Participants

7

Reactant 3

HCID 675612-(Trifluoromethyl)benzoyl chlorideHCID 116163634-(6,7-Dimethoxyquinazolin-4-yloxy)anilineHCID 16776691HCID 16776691, compound

Product 2

HCID 16776691HCID 16776691, compoundHCID 21890190HCID 21890190, compoundYield 56%

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent2×HCID 1140TolueneSolvent

Procedure

2-(Trifluoromethyl)-1-benzenecarbonyl isothiocyanate was prepared using commercially available 2-(trifluoromethyl)-1-benzenecarbonyl chloride (80 mg) as a starting compound according to the description of the literature. 4-[(6,7-Dimethoxy-4-quinazolinyl)oxy]aniline (50 mg) was dissolved in toluene (5 ml) and ethanol (1 ml) to prepare a solution. A solution of 2-(trifluoromethyl)-1-benzenecarbonyl isothiocyanate in ethanol (1 ml) was then added to the solution, and the mixture was stirred at room temperature for 2 hr. The reaction solution was concentrated, and the residue was purified by chromatography on silica gel using chloroform/acetone for development to give the title compound (49 mg, yield 56%).

Workup

  1. concentrationThe reaction solution was concentrated
  2. customthe residue was purified by chromatography on silica gel

Sources & evidence

ORD record
ord-9fb1093cdc9945ec93d0ce3dec97cff7
Source dataset
uspto-grants-2006_11
Patent number
US07135466B2

Reaction notes

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