2-(Trifluoromethyl)benzoyl chloride → HCID 21890182, compound

HRID 721704Notes

Reaction equation

HRID 721704 reaction equation
FC(F)(F)C1C=CC=CC=1C(Cl)=O.[Cl:14][C:15]1[CH:16]=[C:17]([CH:19]=[CH:20][C:21]=1[O:22][C:23]1[C:32]2[C:27](=[CH:28][C:29]([O:35][CH3:36])=[C:30]([O:33][CH3:34])[CH:31]=2)[N:26]=[CH:25][CH:24]=1)[NH2:18].[F:37][C:38]([F:51])([F:50])[C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][C:40]=1[C:45]([N:47]=[C:48]=[S:49])=[O:46]>C1(C)C=CC=CC=1.C(O)C>[F:50][C:38]([F:37])([F:51])[C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][C:40]=1[C:45]([N:47]=[C:48]=[S:49])=[O:46].[Cl:14][C:15]1[CH:16]=[C:17]([NH:18][C:48]([NH:47][C:45](=[O:46])[C:40]2[CH:41]=[CH:42][CH:43]=[CH:44][C:39]=2[C:38]([F:37])([F:51])[F:50])=[S:49])[CH:19]=[CH:20][C:21]=1[O:22][C:23]1[C:32]2[C:27](=[CH:28][C:29]([O:35][CH3:36])=[C:30]([O:33][CH3:34])[CH:31]=2)[N:26]=[CH:25][CH:24]=1

Participants

7

Reactant 3

HCID 675612-(Trifluoromethyl)benzoyl chlorideHCID 117390273-Chloro-4-[(6,7-dimethoxy-4-quinolyl)oxy]anilineHCID 16776691HCID 16776691, compound

Product 2

HCID 16776691HCID 16776691, compoundHCID 21890182HCID 21890182, compoundYield 85%

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. 3-Chloro-4-[(6,7-dimethoxy-4-quinolyl)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 (61 mg, yield 85%).

Workup

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

Sources & evidence

ORD record
ord-552970b44a704cd887a23505cf90d575
Source dataset
uspto-grants-2006_11
Patent number
US07135466B2

Reaction notes

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