Ethanol → N-{4-[(6,7-Dimethoxy-4-quinolyl)oxy]phenyl}-N'-(4-nitrobenzoyl)thiourea

HRID 721739Notes

Reaction equation

HRID 721739 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[N:9]=[CH:8][CH:7]=[C:6]2[O:15][C:16]1[CH:22]=[CH:21][C:19]([NH2:20])=[CH:18][CH:17]=1.C(O)C.[N+:26]([C:29]1[CH:34]=[CH:33][C:32]([C:35]([N:37]=[C:38]=[S:39])=[O:36])=[CH:31][CH:30]=1)([O-:28])=[O:27]>C1(C)C=CC=CC=1>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[N:9]=[CH:8][CH:7]=[C:6]2[O:15][C:16]1[CH:22]=[CH:21][C:19]([NH:20][C:38]([NH:37][C:35](=[O:36])[C:32]2[CH:31]=[CH:30][C:29]([N+:26]([O-:28])=[O:27])=[CH:34][CH:33]=2)=[S:39])=[CH:18][CH:17]=1

Participants

5

Reactant 3

HCID 702EthanolHCID 1413984-Nitrobenzoyl isothiocyanateHCID 115945434-[(6,7-Dimethoxyquinolin-4-yl)oxy]aniline

Product 1

HCID 21889898N-{4-[(6,7-Dimethoxy-4-quinolyl)oxy]phenyl}-N'-(4-nitrobenzoyl)thioureaYield 110%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

4-[(6,7-Dimethoxy-4-quinolyl)oxy]aniline (50 mg) was dissolved in toluene (5 ml) and ethanol (1 ml) to prepare a solution. Commercially available 4-nitro-1-benzenecarbonyl isothiocyanate (30 mg) 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 (80 mg, yield 94%).

Workup

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

Sources & evidence

ORD record
ord-16250940d6f049b4aea01b0024f4355f
Source dataset
uspto-grants-2006_11
Patent number
US07135466B2

Reaction notes

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