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

HRID 721799Notes

Reaction equation

HRID 721799 reaction equation
C1(CC(Cl)=O)CCCCC1.[CH:11]1([CH2:17][C:18]([N:20]=[C:21]=[S:22])=[O:19])[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]1.[CH3:23][O:24][C:25]1[CH:26]=[C:27]2[C:32](=[CH:33][C:34]=1[O:35][CH3:36])[N:31]=[CH:30][CH:29]=[C:28]2[O:37][C:38]1[CH:44]=[CH:43][C:41]([NH2:42])=[CH:40][CH:39]=1.C1(C)C=CC=CC=1>C(O)C>[CH:11]1([CH2:17][C:18]([N:20]=[C:21]=[S:22])=[O:19])[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]1.[CH:11]1([CH2:17][C:18]([NH:20][C:21]([NH:42][C:41]2[CH:43]=[CH:44][C:38]([O:37][C:28]3[C:27]4[C:32](=[CH:33][C:34]([O:35][CH3:36])=[C:25]([O:24][CH3:23])[CH:26]=4)[N:31]=[CH:30][CH:29]=3)=[CH:39][CH:40]=2)=[S:22])=[O:19])[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]1

Participants

7

Reactant 4

HCID 1140TolueneHCID 2757989Cyclohexylacetyl chlorideHCID 115945434-[(6,7-Dimethoxyquinolin-4-yl)oxy]anilineHCID 218904982-Cyclohexylacetyl isothiocyanate

Product 2

HCID 218904982-Cyclohexylacetyl isothiocyanateHCID 21890729N-(2-Cyclohexylacetyl)-N'-{4-[(6,7-dimethoxy-4-quinolyl)oxy]phenyl}thioureaYield 90%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

2-Cyclohexylethanoyl isothiocyanate was prepared using commercially available 2-cyclohexylethanoyl chloride (80 mg) as a starting compound according to the description of the literature. 2-Cyclohexylethanoyl 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 (73 mg, yield 90%).

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-55a4e4b1cbf74d259f2ddeba1d9864b2
Source dataset
uspto-grants-2006_11
Patent number
US07135466B2

Reaction notes

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