Ethanol → N-(2-Chlorobenzoyl)-N'-{3-chloro-4-[(6,7-dimethoxy-4-quinazolinyl)oxy]phenyl}thiourea

HRID 721700Notes

Reaction equation

HRID 721700 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:6]=[CH:7][C:8]=1[O:9][C:10]1[C:19]2[C:14](=[CH:15][C:16]([O:22][CH3:23])=[C:17]([O:20][CH3:21])[CH:18]=2)[N:13]=[CH:12][N:11]=1)[NH2:5].C(O)C.[Cl:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=1[C:34]([N:36]=[C:37]=[S:38])=[O:35]>C1(C)C=CC=CC=1>[Cl:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=1[C:34]([NH:36][C:37]([NH:5][C:4]1[CH:6]=[CH:7][C:8]([O:9][C:10]2[C:19]3[C:14](=[CH:15][C:16]([O:22][CH3:23])=[C:17]([O:20][CH3:21])[CH:18]=3)[N:13]=[CH:12][N:11]=2)=[C:2]([Cl:1])[CH:3]=1)=[S:38])=[O:35]

Participants

5

Reactant 3

HCID 702EthanolHCID 27573982-Chlorobenzoyl isothiocyanateHCID 218905643-Chloro-4-[(6,7-dimethoxy-4-quinazolinyl)oxy]aniline

Product 1

HCID 21889993N-(2-Chlorobenzoyl)-N'-{3-chloro-4-[(6,7-dimethoxy-4-quinazolinyl)oxy]phenyl}thioureaYield 90%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

3-Chloro-4-[(6,7-dimethoxy-4-quinazolinyl)oxy]aniline (50 mg) was dissolved in toluene (5 ml) and ethanol (1 ml) to prepare a solution. Commercially available 2-chloro-1-benzenecarbonyl isothiocyanate (50 μl) 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 (79 mg, yield 90%).

Workup

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

Sources & evidence

ORD record
ord-8edd5bf404c04ce1a7102494e3187cd6
Source dataset
uspto-grants-2006_11
Patent number
US07135466B2

Reaction notes

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