Thionyl Chloride → HCID 21890302, compound

HRID 721593Notes

Reaction equation

HRID 721593 reaction equation
[S:1](Cl)(Cl)=O.[N+:5]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[CH2:14][C:15]([OH:17])=O)([O-:7])=[O:6].[N+:18]([C:21]1C=CC=CC=1CC(Cl)=O)([O-])=O>C1(C)C=CC=CC=1>[N+:5]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[CH2:14][C:15]([N:18]=[C:21]=[S:1])=[O:17])([O-:7])=[O:6]

Participants

5

Reactant 3

HCID 24386Thionyl ChlorideHCID 77337(2-Nitrophenyl)acetic acidHCID 1409562-Nitrobenzeneacetyl chloride

Product 1

HCID 21890302HCID 21890302, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

Toluene (20 ml) and thionyl chloride (1 ml) were added to commercially available 2-(2-nitrophenyl)acetic acid (80 mg), and the mixture was heated at 100° C. for one hr. The solvent was removed by distillation, and 2-(2-nitrophenyl)ethanoyl isothiocyanate was prepared using the resultant 2-(2-nitrophenyl)ethanoyl chloride as a starting compound according to the description of the literature. 2-(2-Nitrophenyl)ethanoyl isothiocyanate thus obtained was dissolved in ethanol (1 ml) to prepare a solution. 3-Chloro-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 16 hr. The reaction solution was concentrated, and the residue was purified by chromatography on silica gel using chloroform/methanol for development to give the title compound (8 mg, yield 10%).

Workup

  1. customThe solvent was removed by distillation, and 2-(2-nitrophenyl)ethanoyl isothiocyanate
  2. customwas prepared

Sources & evidence

ORD record
ord-916c7574315c4e11821922763572e3f1
Source dataset
uspto-grants-2006_11
Patent number
US07135466B2

Reaction notes

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