3,5-Dichlorobenzoyl chloride → N-(3,5-Dichlorobenzoyl)-N'-{4-[(6,7-dimethoxy-4-quinazolinyl)oxy]phenyl}thiourea

HRID 721933Notes

Reaction equation

HRID 721933 reaction equation
ClC1C=C(C(Cl)=O)C=C(Cl)C=1.[CH3:12][O:13][C:14]1[CH:15]=[C:16]2[C:21](=[CH:22][C:23]=1[O:24][CH3:25])[N:20]=[CH:19][N:18]=[C:17]2[O:26][C:27]1[CH:33]=[CH:32][C:30]([NH2:31])=[CH:29][CH:28]=1.[Cl:34][C:35]1[CH:36]=[C:37]([C:42]([N:44]=[C:45]=[S:46])=[O:43])[CH:38]=[C:39]([Cl:41])[CH:40]=1>C1(C)C=CC=CC=1.C(O)C>[Cl:34][C:35]1[CH:36]=[C:37]([C:42]([N:44]=[C:45]=[S:46])=[O:43])[CH:38]=[C:39]([Cl:41])[CH:40]=1.[Cl:34][C:35]1[CH:36]=[C:37]([CH:38]=[C:39]([Cl:41])[CH:40]=1)[C:42]([NH:44][C:45]([NH:31][C:30]1[CH:32]=[CH:33][C:27]([O:26][C:17]2[C:16]3[C:21](=[CH:22][C:23]([O:24][CH3:25])=[C:14]([O:13][CH3:12])[CH:15]=3)[N:20]=[CH:19][N:18]=2)=[CH:28][CH:29]=1)=[S:46])=[O:43]

Participants

7

Reactant 3

HCID 761913,5-Dichlorobenzoyl chlorideHCID 116163634-(6,7-Dimethoxyquinazolin-4-yloxy)anilineHCID 16774862HCID 16774862, compound

Product 2

HCID 16774862HCID 16774862, compoundHCID 21890660N-(3,5-Dichlorobenzoyl)-N'-{4-[(6,7-dimethoxy-4-quinazolinyl)oxy]phenyl}thioureaYield 45%

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent2×HCID 1140TolueneSolvent

Procedure

3,5-Dichloro-1-benzenecarbonyl isothiocyanate was prepared using commercially available 3,5-dichloro-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 3,5-dichloro-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 (40 mg, yield 45%).

Workup

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

Sources & evidence

ORD record
ord-ec548bd942c94ccf99369c65e78e6b78
Source dataset
uspto-grants-2006_11
Patent number
US07135466B2

Reaction notes

Loading…