3-(Trifluoromethyl)benzoyl chloride → N-{4-[(6,7-Dimethoxy-4-quinazolinyl)oxy]phenyl}-N'-[3-(trifluoromethyl)benzoyl]thiourea

HRID 721734Notes

Reaction equation

HRID 721734 reaction equation
FC(F)(F)C1C=C(C(Cl)=O)C=CC=1.[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:39]=[C:40]([C:44]([N:46]=[C:47]=[S:48])=[O:45])[CH:41]=[CH:42][CH:43]=1>C1(C)C=CC=CC=1.C(O)C>[F:49][C:37]([F:36])([F:50])[C:38]1[CH:39]=[C:40]([C:44]([N:46]=[C:47]=[S:48])=[O:45])[CH:41]=[CH:42][CH:43]=1.[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:40]2[CH:41]=[CH:42][CH:43]=[C:38]([C:37]([F:36])([F:50])[F:49])[CH:39]=2)=[S:48])=[CH:31][CH:30]=1

Participants

7

Reactant 3

HCID 752573-(Trifluoromethyl)benzoyl chlorideHCID 116163634-(6,7-Dimethoxyquinazolin-4-yloxy)anilineHCID 217841763-(trifluoromethyl)benzoyl isothiocyanate

Product 2

HCID 217841763-(trifluoromethyl)benzoyl isothiocyanateHCID 21891007N-{4-[(6,7-Dimethoxy-4-quinazolinyl)oxy]phenyl}-N'-[3-(trifluoromethyl)benzoyl]thioureaYield 85%

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent2×HCID 1140TolueneSolvent

Procedure

3-(Trifluoromethyl)-1-benzenecarbonyl isothiocyanate was prepared using commercially available 3-(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 3-(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 (75 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-d1c75313a51144afb0947d82c57b2a18
Source dataset
uspto-grants-2006_11
Patent number
US07135466B2

Reaction notes

Loading…