Реакция #1605867

Уравнение реакции

triethylamine

Oxalyl chloride

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

compound 24e

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

N,O-dimethylhydroxylamine hydrochloride

→

title compound

Выход 53.2%

3-(4-(N-((dimethylamino)methylene)sulfamoyl)phenyl)-N-methoxy-N,4-dimethyl-5-morpholinothiophene-2-carboxamide

Выход 53.2%

Растворители

dichloromethane

dichloromethane

DMF

Условия реакции

Обработка

1. 1
   КонцентрированиеThe reaction mixture was concentrated under reduced pressure
2. 2
   Другоеused directly for further reaction
3. 3
   ДругоеThe residue so obtained
4. 4
   workup.STIRRINGunder stirring at 0° C
5. 5
   workup.STIRRINGThe reaction mixture was stirred at room temperature for 2 hr
6. 6
   ДругоеThe progress of reaction
7. 7
   ПромывкаThe reaction mixture was washed with water (2×10 ml)
8. 8
   Сушкаthe resulting organic layer was dried over anhydrous sodium sulphate
9. 9
   Концентрированиеconcentrated under reduced pressure
10. 10
    Другоеto obtain a crude product
11. 11
    ДругоеThe crude product was further purified by column chromatography over silica gel (100-200 mesh)

Методика

Oxalyl chloride (0.19 g, 0.13 ml, 1.49 mmol) was added dropwise at 0° C. to a solution of 4-methyl-5-morpholino-3-(4-sulfamoylphenyl)thiophene-2-carboxylic acid (compound 24e, 0.19 g, 0.497 mmol) in a mixture of dichloromethane (15 ml) and DMF (0.073 g, 0.08 ml, 0.99 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 the 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 (15 ml) and to this was added triethylamine (0.251 g, 0.35 ml, 2.48 mmol) followed by the addition of N,O-dimethylhydroxylamine hydrochloride (0.098 g, 0.99 mmol) under stirring at 0° C. 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 (2×10 ml) and the resulting organic layer 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 1% methanol in dichloromethane as an eluent to obtain the title compound (0.127 g, 53%).

Источник