Toluene → N-{3-Chloro-4-[(6,7-dimethoxy-4-quinolyl)oxy]phenyl}-N'-[(2-phenylcyclopropyl)carbonyl]thiourea

HRID 721835Notes

Reaction equation

HRID 721835 reaction equation
C1(C2CC2C(Cl)=O)C=CC=CC=1.[C:13]1([CH:19]2[CH2:21][CH:20]2[C:22]([N:24]=[C:25]=[S:26])=[O:23])[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.[Cl:27][C:28]1[CH:29]=[C:30]([CH:32]=[CH:33][C:34]=1[O:35][C:36]1[C:45]2[C:40](=[CH:41][C:42]([O:48][CH3:49])=[C:43]([O:46][CH3:47])[CH:44]=2)[N:39]=[CH:38][CH:37]=1)[NH2:31].C1(C)C=CC=CC=1>C(O)C>[C:13]1([CH:19]2[CH2:21][CH:20]2[C:22]([N:24]=[C:25]=[S:26])=[O:23])[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.[Cl:27][C:28]1[CH:29]=[C:30]([NH:31][C:25]([NH:24][C:22]([CH:20]2[CH2:21][CH:19]2[C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[O:23])=[S:26])[CH:32]=[CH:33][C:34]=1[O:35][C:36]1[C:45]2[C:40](=[CH:41][C:42]([O:48][CH3:49])=[C:43]([O:46][CH3:47])[CH:44]=2)[N:39]=[CH:38][CH:37]=1

Participants

7

Reactant 4

HCID 1140TolueneHCID 523092Cyclopropanecarbonyl chloride, 2-phenyl-HCID 117390273-Chloro-4-[(6,7-dimethoxy-4-quinolyl)oxy]anilineHCID 218907262-Phenyl-1-cyclopropanecarbonyl isothiocyanate

Product 2

HCID 21889869N-{3-Chloro-4-[(6,7-dimethoxy-4-quinolyl)oxy]phenyl}-N'-[(2-phenylcyclopropyl)carbonyl]thioureaYield 60%HCID 218907262-Phenyl-1-cyclopropanecarbonyl isothiocyanate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

2-Phenyl-1-cyclopropanecarbonyl isothiocyanate was prepared using commercially available 2-phenyl-1-cyclopropanecarbonyl chloride (80 mg) as a starting compound according to the description of the literature. 2-Phenyl-1-cyclopropanecarbonyl isothiocyanate was dissolved in ethanol (1 ml) to prepare a solution. 3-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 (48 mg, yield 60%).

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-b2950e047f9140f7bc4dd7233f07852a
Source dataset
uspto-grants-2006_11
Patent number
US07135466B2

Reaction notes

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