4-(Chloromethyl)benzoyl chloride → N-[4-(Chloromethyl)benzoyl]-N'-{4-[(6,7-dimethoxy-4-quinolyl)oxy]phenyl}thiourea

HRID 721910Notes

Reaction equation

HRID 721910 reaction equation
ClCC1C=CC(C(Cl)=O)=CC=1.[CH3:12][O:13][C:14]1[CH:15]=[C:16]2[C:21](=[CH:22][C:23]=1[O:24][CH3:25])[N:20]=[CH:19][CH:18]=[C:17]2[O:26][C:27]1[CH:33]=[CH:32][C:30]([NH2:31])=[CH:29][CH:28]=1.[Cl:34][CH2:35][C:36]1[CH:41]=[CH:40][C:39]([C:42]([N:44]=[C:45]=[S:46])=[O:43])=[CH:38][CH:37]=1>C1(C)C=CC=CC=1.C(O)C>[Cl:34][CH2:35][C:36]1[CH:37]=[CH:38][C:39]([C:42]([N:44]=[C:45]=[S:46])=[O:43])=[CH:40][CH:41]=1.[Cl:34][CH2:35][C:36]1[CH:37]=[CH:38][C:39]([C:42]([NH:44][C:45]([NH:31][C:30]2[CH:32]=[CH:33][C:27]([O:26][C:17]3[C:16]4[C:21](=[CH:22][C:23]([O:24][CH3:25])=[C:14]([O:13][CH3:12])[CH:15]=4)[N:20]=[CH:19][CH:18]=3)=[CH:28][CH:29]=2)=[S:46])=[O:43])=[CH:40][CH:41]=1

Participants

7

Reactant 3

HCID 701364-(Chloromethyl)benzoyl chlorideHCID 115945434-[(6,7-Dimethoxyquinolin-4-yl)oxy]anilineHCID 21890761HCID 21890761, compound

Product 2

HCID 21890761HCID 21890761, compoundHCID 21891065N-[4-(Chloromethyl)benzoyl]-N'-{4-[(6,7-dimethoxy-4-quinolyl)oxy]phenyl}thioureaYield 63%

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent2×HCID 1140TolueneSolvent

Procedure

4-(Chloromethyl)-1-benzenecarbonyl isothiocyanate was prepared using commercially available 4-(chloromethyl)-1-benzenecarbonyl chloride (80 mg) as a starting compound according to the description of the literature. 4-[(6,7-Dimethoxy-4-quinolyl)oxy]aniline (50 mg) was dissolved in toluene (5 ml) and ethanol (1 ml) to prepare a solution. A solution of 4-(chloromethyl)-1-benzenecarbonyl 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 (54 mg, yield 63%).

Workup

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

Sources & evidence

ORD record
ord-5918029624ae48a6934efde30c795b57
Source dataset
uspto-grants-2006_11
Patent number
US07135466B2

Reaction notes

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