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

HRID 721840Notes

Reaction equation

HRID 721840 reaction equation
[CH:1]1(C(Cl)=O)CCCCC1.[CH:10]1([C:16]([N:18]=[C:19]=[S:20])=[O:17])[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]1.[CH3:21][O:22][C:23]1[CH:24]=[C:25]2[C:30](=[CH:31][C:32]=1[O:33][CH3:34])[N:29]=[CH:28]N=[C:26]2[O:35][C:36]1[CH:42]=[CH:41][C:39]([NH2:40])=[C:38]([F:43])[CH:37]=1.C1(C)C=CC=CC=1>C(O)C>[CH:10]1([C:16]([N:18]=[C:19]=[S:20])=[O:17])[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]1.[CH:10]1([C:16]([NH:18][C:19]([NH:40][C:39]2[CH:41]=[CH:42][C:36]([O:35][C:26]3[C:25]4[C:30](=[CH:31][C:32]([O:33][CH3:34])=[C:23]([O:22][CH3:21])[CH:24]=4)[N:29]=[CH:28][CH:1]=3)=[CH:37][C:38]=2[F:43])=[S:20])=[O:17])[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]1

Participants

7

Reactant 4

HCID 1140TolueneHCID 75938Cyclohexanecarbonyl chlorideHCID 6993632Cyclohexanecarbonyl isothiocyanateHCID 218902744-((6,7-Dimethoxy-4-quinazolinyl)oxy]-2-fluoroaniline

Product 2

HCID 6993632Cyclohexanecarbonyl isothiocyanateHCID 21890745N-Cyclohexylcarbonyl-N'-{4-[(6,7-dimethoxy-4-quinolyl)oxy]-2-fluorophenyl}thioureaYield 61%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

1-Cyclohexanecarbonyl isothiocyanate was prepared using commercially available 1-cyclohexanecarbonyl chloride (80 mg) as a starting compound according to the description of the literature. 1-Cyclohexanecarbonyl isothiocyanate was dissolved in ethanol (1 ml) to prepare a solution. 4-[(6,7-Dimethoxy-4-quinazolinyl)oxy]-2-fluoroaniline (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 (47 mg, yield 61%).

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-9781b67ecb414ece895f7491de4e1a10
Source dataset
uspto-grants-2006_11
Patent number
US07135466B2

Reaction notes

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