Toluene → N-{2-Chloro-4-[(6,7-dimethoxy-4-quinolyl)oxy]phenyl}-N'-(2-methoxybenzoyl)thiourea

HRID 721878Notes

Reaction equation

HRID 721878 reaction equation
COC1C=CC=CC=1C(Cl)=O.[CH3:12][O:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[C:20]([N:22]=[C:23]=[S:24])=[O:21].[Cl:25][C:26]1[CH:32]=[C:31]([O:33][C:34]2[C:43]3[C:38](=[CH:39][C:40]([O:46][CH3:47])=[C:41]([O:44][CH3:45])[CH:42]=3)[N:37]=[CH:36][CH:35]=2)[CH:30]=[CH:29][C:27]=1[NH2:28].C1(C)C=CC=CC=1>C(O)C>[CH3:12][O:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[C:20]([N:22]=[C:23]=[S:24])=[O:21].[Cl:25][C:26]1[CH:32]=[C:31]([O:33][C:34]2[C:43]3[C:38](=[CH:39][C:40]([O:46][CH3:47])=[C:41]([O:44][CH3:45])[CH:42]=3)[N:37]=[CH:36][CH:35]=2)[CH:30]=[CH:29][C:27]=1[NH:28][C:23]([NH:22][C:20](=[O:21])[C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=1[O:13][CH3:12])=[S:24]

Participants

7

Reactant 4

HCID 1140TolueneHCID 889692-Methoxybenzoyl chlorideHCID 112212234-[(6,7-Dimethoxy-4-quinolyl)oxy]-2-chloroanilineHCID 143631602-Methoxybenzoyl isothiocyanate

Product 2

HCID 143631602-Methoxybenzoyl isothiocyanateHCID 21889861N-{2-Chloro-4-[(6,7-dimethoxy-4-quinolyl)oxy]phenyl}-N'-(2-methoxybenzoyl)thioureaYield 45%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

2-Methoxy-1-benzenecarbonyl isothiocyanate was prepared using commercially available 2-methoxy-1-benzenecarbonyl chloride (80 mg) as a starting compound according to the description of the literature. 2-Methoxy-1-benzenecarbonyl isothiocyanate was dissolved in ethanol (1 ml) to prepare a solution. 2-Chloro-4-[(6,7-dimethoxy-4-quinolyl)oxy]aniline (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 (36 mg, yield 45%).

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-f1822c58785941378f14040c386d95ba
Source dataset
uspto-grants-2006_11
Patent number
US07135466B2

Reaction notes

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