4-Bromobenzoyl chloride → N-(4-Bromobenzoyl)-N'-{4-[(6,7-dimethoxy-4-quinazolinyl)oxy]phenyl}thiourea

HRID 721943Notes

Reaction equation

HRID 721943 reaction equation
BrC1C=CC(C(Cl)=O)=CC=1.[CH3:11][O:12][C:13]1[CH:14]=[C:15]2[C:20](=[CH:21][C:22]=1[O:23][CH3:24])[N:19]=[CH:18][N:17]=[C:16]2[O:25][C:26]1[CH:32]=[CH:31][C:29]([NH2:30])=[CH:28][CH:27]=1.[Br:33][C:34]1[CH:39]=[CH:38][C:37]([C:40]([N:42]=[C:43]=[S:44])=[O:41])=[CH:36][CH:35]=1>C1(C)C=CC=CC=1.C(O)C>[Br:33][C:34]1[CH:35]=[CH:36][C:37]([C:40]([N:42]=[C:43]=[S:44])=[O:41])=[CH:38][CH:39]=1.[Br:33][C:34]1[CH:39]=[CH:38][C:37]([C:40]([NH:42][C:43]([NH:30][C:29]2[CH:31]=[CH:32][C:26]([O:25][C:16]3[C:15]4[C:20](=[CH:21][C:22]([O:23][CH3:24])=[C:13]([O:12][CH3:11])[CH:14]=4)[N:19]=[CH:18][N:17]=3)=[CH:27][CH:28]=2)=[S:44])=[O:41])=[CH:36][CH:35]=1

Participants

7

Reactant 3

HCID 685154-Bromobenzoyl chlorideHCID 2449954-bromobenzoyl isothiocyanateHCID 116163634-(6,7-Dimethoxyquinazolin-4-yloxy)aniline

Product 2

HCID 2449954-bromobenzoyl isothiocyanateHCID 21890399N-(4-Bromobenzoyl)-N'-{4-[(6,7-dimethoxy-4-quinazolinyl)oxy]phenyl}thioureaYield 58%

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent2×HCID 1140TolueneSolvent

Procedure

4-Bromo-1-benzenecarbonyl isothiocyanate was prepared using commercially available 4-bromo-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 4-bromo-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 (53 mg, yield 58%).

Workup

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

Sources & evidence

ORD record
ord-ec1c0b1ccfcd40e09f2e90ba99bfa756
Source dataset
uspto-grants-2006_11
Patent number
US07135466B2

Reaction notes

Loading…