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

HRID 721831Notes

Reaction equation

HRID 721831 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.[CH3:27][O:28][C:29]1[CH:30]=[C:31]2[C:36](=[CH:37][C:38]=1[O:39][CH3:40])[N:35]=[CH:34][CH:33]=[C:32]2[O:41][C:42]1[CH:48]=[CH:47][C:45]([NH2:46])=[CH:44][CH:43]=1.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.[CH3:27][O:28][C:29]1[CH:30]=[C:31]2[C:36](=[CH:37][C:38]=1[O:39][CH3:40])[N:35]=[CH:34][CH:33]=[C:32]2[O:41][C:42]1[CH:43]=[CH:44][C:45]([NH:46][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:47][CH:48]=1

Participants

7

Reactant 4

HCID 1140TolueneHCID 523092Cyclopropanecarbonyl chloride, 2-phenyl-HCID 115945434-[(6,7-Dimethoxyquinolin-4-yl)oxy]anilineHCID 218907262-Phenyl-1-cyclopropanecarbonyl isothiocyanate

Product 2

HCID 218907262-Phenyl-1-cyclopropanecarbonyl isothiocyanateHCID 21890739N-{4-[(6,7-Dimethoxy-4-quinolyl)oxy]phenyl}-N'-[(2-phenylcyclopropyl)carbonyl]thioureaYield 63%

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. 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 (53 mg, yield 63%).

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-92daa9d74d8c491c8f64462c85f4c851
Source dataset
uspto-grants-2006_11
Patent number
US07135466B2

Reaction notes

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