Ethanol → N-{4-[(6,7-Dimethoxy-4-quinolyl)oxy]-2-nitrophenyl}-N'-(3-methylbenzoyl)thiourea

HRID 721730

Reaction equation

HRID 721730 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])=[C:18]([N+:23]([O-:25])=[O:24])[CH:17]=1.C(O)C.[CH3:29][C:30]1[CH:31]=[C:32]([C:36]([N:38]=[C:39]=[S:40])=[O:37])[CH:33]=[CH:34][CH:35]=1>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:39]([NH:38][C:36](=[O:37])[C:32]2[CH:33]=[CH:34][CH:35]=[C:30]([CH3:29])[CH:31]=2)=[S:40])=[C:18]([N+:23]([O-:25])=[O:24])[CH:17]=1

Participants

5

Reactant 3

HCID 702EthanolHCID 1413973-Methylbenzoyl isothiocyanateHCID 218907304-[(6,7-Dimethoxy-4-quinolyl)oxy]-2-nitroaniline

Product 1

HCID 21890175N-{4-[(6,7-Dimethoxy-4-quinolyl)oxy]-2-nitrophenyl}-N'-(3-methylbenzoyl)thioureaYield 91%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

4-[(6,7-Dimethoxy-4-quinolyl)oxy]-2-nitroaniline (50 mg) was dissolved in toluene (5 ml) and ethanol (1 ml) to prepare a solution. Commercially available 3-methyl-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 (69 mg, yield 91%).

Workup

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

Sources & evidence

ORD record
ord-101f76f6918c44a2a98d0ade87750a27
Source dataset
uspto-grants-2006_11
Patent number
US07135466B2

Linked notes

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