Реакция #2357320

Уравнение реакции

methyl 4-amino-2-(N-tert-butylsulfamoyl)benzoate

sodium acetate

ethyl nitroacetate

ethanol

sodium nitrite

→

methyl 2-(N-tert-butylsulfamoyl)-4-(ethoxycarbonylnitromethylenehydrazino)benzoate

Выход 60.0%

Растворители

HCl

water

water

water

Условия реакции

Обработка

1. 1
   ФильтрацияThe few undissolved components are filtered off cold
2. 2
   workup.WAITthe mixture is left
3. 3
   workup.WAITto stand at this temperature for 15 h
4. 4
   ФильтрацияThe mixture is filtered off
5. 5
   Промывкаthe solid is washed with water
6. 6
   Другоеdried under reduced pressure

Методика

5.7 g (0.02 mol) of methyl 4-amino-2-(N-tert-butylsulfamoyl)benzoate are suspended in a mixture of 30 ml of conc. HCl and 36 ml of water. At 0-50° C., a solution of 1.5 g (0.022 mol) of sodium nitrite in 9 ml of water is added dropwise. The few undissolved components are filtered off cold, and the cold diazonium salt solution is slowly poured, at 5-10° C., into a mixture of 8.9 g (0.11 mol) of sodium acetate, 16 ml of water, 60 ml of ethanol and 2.7 g (0.02 mol) of ethyl nitroacetate. Stirring is continued at 0° C. for 2 h and the mixture is left to stand at this temperature for 15 h. The mixture is filtered off and the solid is washed with water and dried under reduced pressure, giving 5.2 g (60% of theory) of methyl 2-(N-tert-butylsulfamoyl)-4-(ethoxycarbonylnitromethylenehydrazino)benzoate of m.p. 142-145° C.

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