4-Butylbenzoyl chloride → HCID 21889966, compound

HRID 721771Notes

Reaction equation

HRID 721771 reaction equation
C(C1C=CC(C(Cl)=O)=CC=1)CCC.[CH3:14][O:15][C:16]1[CH:17]=[C:18]2[C:23](=[CH:24][C:25]=1[O:26][CH3:27])[N:22]=[CH:21][CH:20]=[C:19]2[O:28][C:29]1[CH:35]=[CH:34][C:32]([NH2:33])=[C:31]([F:36])[CH:30]=1.[CH2:37]([C:41]1[CH:46]=[CH:45][C:44]([C:47]([N:49]=[C:50]=[S:51])=[O:48])=[CH:43][CH:42]=1)[CH2:38][CH2:39][CH3:40]>C1(C)C=CC=CC=1.C(O)C>[CH2:37]([C:41]1[CH:46]=[CH:45][C:44]([C:47]([N:49]=[C:50]=[S:51])=[O:48])=[CH:43][CH:42]=1)[CH2:38][CH2:39][CH3:40].[CH2:37]([C:41]1[CH:46]=[CH:45][C:44]([C:47]([NH:49][C:50]([NH:33][C:32]2[CH:34]=[CH:35][C:29]([O:28][C:19]3[C:18]4[C:23](=[CH:24][C:25]([O:26][CH3:27])=[C:16]([O:15][CH3:14])[CH:17]=4)[N:22]=[CH:21][CH:20]=3)=[CH:30][C:31]=2[F:36])=[S:51])=[O:48])=[CH:43][CH:42]=1)[CH2:38][CH2:39][CH3:40]

Participants

7

Reactant 3

HCID 1200494-Butylbenzoyl chlorideHCID 113014704-[(6,7-Dimethoxy-4-quinolyl)oxy]-2-fluoroanilineHCID 21890188HCID 21890188, compound

Product 2

HCID 21889966HCID 21889966, compoundYield 80%HCID 21890188HCID 21890188, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent2×HCID 1140TolueneSolvent

Procedure

4-Butyl-1-benzenecarbonyl isothiocyanate was prepared using commercially available 4-butyl-1-benzenecarbonyl chloride (80 mg) as a starting compound according to the description of the literature. 4-[(6,7-Dimethoxy-4-quinolyl)oxy]-2-fluoroaniline (50 mg) was dissolved in toluene (5 ml) and ethanol (1 ml) to prepare a solution. A solution of 4-butyl-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 (68 mg, yield 80%).

Workup

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

Sources & evidence

ORD record
ord-caf8364ca80d48e1bdbfaf903b553808
Source dataset
uspto-grants-2006_11
Patent number
US07135466B2

Reaction notes

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