Реакция #1605862

Уравнение реакции

triethylamine

Oxalyl chloride

5-(4-chlorophenyl)-4-methyl-3-(4-sulfamoylphenyl)thiophene-2-carboxylic acid

compound 1c

5-(4-chlorophenyl)-4-methyl-3-(4-sulfamoylphenyl)thiophene-2-carboxylic acid

N,O-dimethylhydroxylamine hydrochloride

→

title compound

Выход 86.4%

5-(4-chlorophenyl)-3-(4-(N-((dimethylamino)methylene)sulfamoyl)phenyl)-N-methoxy-N,4-dimethylthiophene-2-carboxamide

Выход 86.4%

Растворители

dichloromethane

dichloromethane

DMF

Условия реакции

Обработка

1. 1
   ДругоеThe progress of reaction
2. 2
   КонцентрированиеThe reaction mixture was concentrated under reduced pressure
3. 3
   Другоеused directly for further reaction
4. 4
   ДругоеThe residue so obtained
5. 5
   workup.STIRRINGunder stirring
6. 6
   workup.STIRRINGThe reaction mixture was stirred at room temperature for 2 hr
7. 7
   ДругоеThe progress of reaction
8. 8
   ПромывкаThe reaction mixture was washed with water (2×20 ml)
9. 9
   Другоеthe organic layer obtained
10. 10
    Сушкаwas dried over anhydrous sodium sulphate
11. 11
    Концентрированиеconcentrated under reduced pressure
12. 12
    Другоеto obtain a crude product
13. 13
    ДругоеThe crude product was further purified by column chromatography over silica gel (100-200 mesh)

Методика

Oxalyl chloride (2.1 g, 1.4 ml, 16.2 mmol) was added dropwise at 0° C. to a solution of 5-(4-chlorophenyl)-4-methyl-3-(4-sulfamoylphenyl)thiophene-2-carboxylic acid (compound 1c, 2.2 g, 5.4 mmol) in a mixture of dichloromethane (40 ml) and DMF (0.8 g, 0.8 ml, 10.8 m mol). The resulting mixture was allowed to warm to room temperature and stirred for 1.5 hr, under a nitrogen atmosphere. The progress of reaction was monitored by TLC. The reaction mixture was concentrated under reduced pressure and used directly for further reaction. The residue so obtained was dissolved in dry dichloromethane (40 ml) and to this was added triethylamine (2.8 g, 3.9 ml, 27.0 mmol) followed by the addition of N,O-dimethylhydroxylamine hydrochloride (1.06 g, 10.8 mmol) under stirring. The reaction mixture was stirred at room temperature for 2 hr. The progress of reaction was monitored by TLC. The reaction mixture was washed with water (2×20 ml) and the organic layer obtained was dried over anhydrous sodium sulphate, and concentrated under reduced pressure to obtain a crude product. The crude product was further purified by column chromatography over silica gel (100-200 mesh) using 80% ethylacetate in hexane as an eluent to obtain the title compound (2.36 g, 86%).

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