Реакция #1605865

Уравнение реакции

ethyl iodoacetate

N,N-dimethyl-N′-((4-(2-methyl-3-morpholino-3-thioxopropanoyl)phenyl)sulfonyl)formimidamide

compound 24c

N,N-dimethyl-N′-((4-(2-methyl-3-morpholino-3-thioxopropanoyl)phenyl)sulfonyl)formimidamide

potassium carbonate

→

title compound

Выход 43.4%

ethyl-3-(4-(N-((dimethylamino)methylene) sulfamoyl)phenyl)-4-methyl-5-morpholinothiophene-2-carboxylate

Выход 43.4%

Растворители

acetone

Условия реакции

Обработка

1. 1
   ТемператураThe reaction mixture was cooled to 0° C.
2. 2
   workup.STIRRINGThe reaction mixture was stirred
3. 3
   Температураat reflux temperature for 4 hr
4. 4
   Температураto warm to room temperature
5. 5
   Фильтрацияfiltered through a celite pad
6. 6
   ПромывкаThe celite pad was washed with acetone (2×10 ml)
7. 7
   КонцентрированиеThe filtrate was concentrated under reduced pressure
8. 8
   Другоеto obtain a crude product, which
9. 9
   Другоеwas purified by column chromatography over silica gel (100-200 mesh)

Методика

To a stirred solution of N,N-dimethyl-N′-((4-(2-methyl-3-morpholino-3-thioxopropanoyl)phenyl)sulfonyl)formimidamide (compound 24c, 0.180 g, 0.45 mmol) in dry acetone (15 ml) was added potassium carbonate (0.45 g, 3.17 mmol) at room temperature. The resulting mixture was stirred at 55-60° C. for 2 hr. The reaction mixture was cooled to 0° C. and to this was added ethyl iodoacetate (0.097 g, 0.053 ml, 0.45 mmol) in a dropwise manner. The reaction mixture was stirred at reflux temperature for 4 hr. The progress of the reaction was monitored by TLC. The reaction mixture was allowed to warm to room temperature and filtered through a celite pad. The celite pad was washed with acetone (2×10 ml). The filtrate was concentrated under reduced pressure to obtain a crude product, which was purified by column chromatography over silica gel (100-200 mesh) using 50-55% ethyl acetate in hexanes as an eluent to obtain the title compound (0.091 g, 43%)

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