Toluene → N-Benzoyl-N'-{4-[(6,7-dimethoxy-4-quinolyl)oxy]-3-methylphenyl}thiourea

HRID 721884Notes

Reaction equation

HRID 721884 reaction equation
[C:1]1([C:7]([N:9]=[C:10]=[S:11])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=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][CH:18]=[C:17]2[O:26][C:27]1[CH:33]=[CH:32][C:30]([NH2:31])=[CH:29][C:28]=1[CH3:34].C1(C)C=CC=CC=1>C(O)C>[C:7]([NH:9][C:10]([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][CH:18]=2)=[C:28]([CH3:34])[CH:29]=1)=[S:11])(=[O:8])[C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 1140TolueneHCID 68284Benzoyl isothiocyanateHCID 218911624-[(6,7-Dimethoxy-4-quinolyl)oxy]-3-methyl-aniline

Product 1

HCID 21889930N-Benzoyl-N'-{4-[(6,7-dimethoxy-4-quinolyl)oxy]-3-methylphenyl}thioureaYield 80%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

Commercially available 1-benzenecarbonyl isothiocyanate (50 μl) was dissolved in ethanol (1 ml) to prepare a solution. 4-[(6,7-Dimethoxy-4-quinolyl)oxy]-3-methylaniline (50 mg), toluene (5 ml), and ethanol (1 ml) were 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 (61 mg, yield 80%).

Workup

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

Sources & evidence

ORD record
ord-f58c01f8a4c9431e9019c43cbd2ca706
Source dataset
uspto-grants-2006_11
Patent number
US07135466B2

Reaction notes

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