Toluene → N-(4-Chlorobutanoyl)-N'-{4-[(6,7-dimethoxy-4-quinolyl)oxy]-3-fluorophenyl}thiourea

HRID 721844Notes

Reaction equation

HRID 721844 reaction equation
Cl[CH2:2]CCC(Cl)=O.[Cl:8][CH2:9][CH2:10][CH2:11][C:12]([N:14]=[C:15]=[S:16])=[O:13].[CH3:17][O:18][C:19]1[CH:20]=[C:21]2[C:26](=[CH:27][C:28]=1[O:29][CH3:30])[N:25]=[CH:24]N=[C:22]2[O:31][C:32]1[CH:38]=[CH:37][C:35]([NH2:36])=[CH:34][C:33]=1[F:39].C1(C)C=CC=CC=1>C(O)C>[Cl:8][CH2:9][CH2:10][CH2:11][C:12]([N:14]=[C:15]=[S:16])=[O:13].[Cl:8][CH2:9][CH2:10][CH2:11][C:12]([NH:14][C:15]([NH:36][C:35]1[CH:37]=[CH:38][C:32]([O:31][C:22]2[C:21]3[C:26](=[CH:27][C:28]([O:29][CH3:30])=[C:19]([O:18][CH3:17])[CH:20]=3)[N:25]=[CH:24][CH:2]=2)=[C:33]([F:39])[CH:34]=1)=[S:16])=[O:13]

Participants

7

Reactant 4

HCID 1140TolueneHCID 783704-Chlorobutyryl chlorideHCID 218906484-Chlorobutanoyl isothiocyanateHCID 218912194-((6,7-Dimethoxyquinazolin-4-yl)oxy)-3-fluoroaniline

Product 2

HCID 21890524N-(4-Chlorobutanoyl)-N'-{4-[(6,7-dimethoxy-4-quinolyl)oxy]-3-fluorophenyl}thioureaYield 54%HCID 218906484-Chlorobutanoyl isothiocyanate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

4-Chlorobutanoyl isothiocyanate was prepared using commercially available 4-chlorobutanoyl chloride (80 mg) as a starting compound according to the description of the literature. 4-Chlorobutanoyl isothiocyanate was dissolved in ethanol (1 ml) to prepare a solution. 4-[(6,7-Dimethoxy-4-quinazolinyl)oxy]-3-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 (41 mg, yield 54%).

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-9892f3572dc04bbfb70b58a4b85eb9a9
Source dataset
uspto-grants-2006_11
Patent number
US07135466B2

Reaction notes

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