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

HRID 721916Notes

Reaction equation

HRID 721916 reaction equation
C1(C2CC2C(Cl)=O)C=CC=CC=1.[CH3:13][O:14][C:15]1[CH:16]=[C:17]2[C:22](=[CH:23][C:24]=1[O:25][CH3:26])[N:21]=[CH:20][CH:19]=[C:18]2[O:27][C:28]1[CH:33]=[CH:32][C:31]([NH:34][CH2:35][CH3:36])=[CH:30][CH:29]=1.[C:37]1([CH:43]2[CH2:45][CH:44]2[C:46]([N:48]=[C:49]=[S:50])=[O:47])[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1>C1(C)C=CC=CC=1.C(O)C>[C:37]1([CH:43]2[CH2:45][CH:44]2[C:46]([N:48]=[C:49]=[S:50])=[O:47])[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1.[CH3:13][O:14][C:15]1[CH:16]=[C:17]2[C:22](=[CH:23][C:24]=1[O:25][CH3:26])[N:21]=[CH:20][CH:19]=[C:18]2[O:27][C:28]1[CH:33]=[CH:32][C:31]([N:34]([CH2:35][CH3:36])[C:49]([NH:48][C:46]([CH:44]2[CH2:45][CH:43]2[C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)=[O:47])=[S:50])=[CH:30][CH:29]=1

Participants

7

Reactant 3

HCID 523092Cyclopropanecarbonyl chloride, 2-phenyl-HCID 218907262-Phenyl-1-cyclopropanecarbonyl isothiocyanateHCID 21891226N-{4-[(6,7-Dimethoxy-4-quinolyl)oxy]phenyl}-N-ethylamine

Product 2

HCID 218907262-Phenyl-1-cyclopropanecarbonyl isothiocyanateHCID 72407261N-{4-[(6,7-Dimethoxy-4-quinolyl)oxy]phenyl}-N-ethyl-N'-[(2-phenylcyclopropyl)carbonyl]thioureaYield 53%

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent2×HCID 1140TolueneSolvent

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. N-{4-[(6,7-Dimethoxy-4-quinolyl)oxy]phenyl}-N-ethylamine (50 mg) was dissolved in toluene (5 ml) and ethanol (1 ml) to prepare a solution. A solution of 2-phenyl-1-cyclopropanecarbonyl isothiocyanate in ethanol (1 ml) 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 (43 mg, yield 53%).

Workup

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

Sources & evidence

ORD record
ord-3fcea6a5dd0d4d86b507d1bd7d04d35a
Source dataset
uspto-grants-2006_11
Patent number
US07135466B2

Reaction notes

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