Benzoyl chloride, 3-bromo- → N-(3-Bromobenzoyl)-N'-{3-chloro-4-[(6,7-dimethoxy-4-quinolyl)oxy]phenyl}thiourea

HRID 721729Notes

Reaction equation

HRID 721729 reaction equation
BrC1C=C(C(Cl)=O)C=CC=1.[Cl:11][C:12]1[CH:13]=[C:14]([CH:16]=[CH:17][C:18]=1[O:19][C:20]1[C:29]2[C:24](=[CH:25][C:26]([O:32][CH3:33])=[C:27]([O:30][CH3:31])[CH:28]=2)[N:23]=[CH:22][CH:21]=1)[NH2:15].[Br:34][C:35]1[CH:36]=[C:37]([C:41]([N:43]=[C:44]=[S:45])=[O:42])[CH:38]=[CH:39][CH:40]=1>C1(C)C=CC=CC=1.C(O)C>[Br:34][C:35]1[CH:36]=[C:37]([C:41]([N:43]=[C:44]=[S:45])=[O:42])[CH:38]=[CH:39][CH:40]=1.[Br:34][C:35]1[CH:36]=[C:37]([CH:38]=[CH:39][CH:40]=1)[C:41]([NH:43][C:44]([NH:15][C:14]1[CH:16]=[CH:17][C:18]([O:19][C:20]2[C:29]3[C:24](=[CH:25][C:26]([O:32][CH3:33])=[C:27]([O:30][CH3:31])[CH:28]=3)[N:23]=[CH:22][CH:21]=2)=[C:12]([Cl:11])[CH:13]=1)=[S:45])=[O:42]

Participants

7

Reactant 3

HCID 74377Benzoyl chloride, 3-bromo-HCID 117390273-Chloro-4-[(6,7-dimethoxy-4-quinolyl)oxy]anilineHCID 156505093-Bromobenzoyl isothiocyanate

Product 2

HCID 156505093-Bromobenzoyl isothiocyanateHCID 21889872N-(3-Bromobenzoyl)-N'-{3-chloro-4-[(6,7-dimethoxy-4-quinolyl)oxy]phenyl}thioureaYield 93%

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent2×HCID 1140TolueneSolvent

Procedure

3-Bromo-1-benzenecarbonyl isothiocyanate was prepared using commercially available 3-bromo-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 3-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 (81 mg, yield 93%).

Workup

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

Sources & evidence

ORD record
ord-00311d0db92b48f390e8a2eb89f5461b
Source dataset
uspto-grants-2006_11
Patent number
US07135466B2

Reaction notes

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