Реакция #2487413

Уравнение реакции

Diethyldithiocarbamic acid

sodium

4-Chloromethylbenzoic acid

carbamic acid

→

1-((diethylcarbamothioylthio)methyl)benzoic Acid

Выход 62.0%

Растворители

ethanol

ethanol

Условия реакции

Обработка

1. 1
   workup.STIRRINGstirred overnight at r.t
2. 2
   ДругоеThe reaction mixture was then evaporated to dryness
3. 3
   Другоеseparated between dichloromethane and brine
4. 4
   ДругоеThe aqueous layer was separated
5. 5
   ДругоеThe precipitate that formed on acidification
6. 6
   Фильтрацияwas filtered
7. 7
   Другоеair-dried
8. 8
   Другоеto give a white solid, 4.1 g (yield 62%)

Методика

4-Chloromethylbenzoic acid (4 g, 0.0234 mol, 1.0 equiv.) was dissolved in warm ethanol (20 mL). Diethyldithiocarbamic acid, sodium salt trihydrate (7.92 g, 0.0328 mol, 1.5 equiv.) was also separately dissolved in warm ethanol (20 mL). The solution of the carbamic acid was then added to the solution of the carboxylic acid. The resulting mixture was then stirred at 40-50° C. for 2 h, then stirred overnight at r.t. The reaction mixture was then evaporated to dryness and separated between dichloromethane and brine. The aqueous layer was separated and acidified with conc. HCl to a pH value of 2. The precipitate that formed on acidification was filtered and air-dried to give a white solid, 4.1 g (yield 62%). 1H NMR (acetone-d6, 400 MHz) δ 1.26, br. s, 6H, 2×CH3; 3.82, br. s, 2H, CH2N, 4.5, br. s, 2H, CH2N, 4.67, s, 2H, CH2S; 7.56 (d, J=8 Hz, 2H, aromatic); 7.98 (d, J=8 Hz, 2H, aromatic) ppm. 13C NMR (acetone-d6, 400 MHz) δ 11.78, 12.98, 41.53, 47.55, 50.45, 130.26, 130.45, 130.69, 143.74, 167.40, 194.94 ppm.

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