反应 #2487413

反应方程式

Diethyldithiocarbamic acid

sodium

4-Chloromethylbenzoic acid

carbamic acid

→

1-((diethylcarbamothioylthio)methyl)benzoic Acid

收率 62.0%

溶剂

ethanol

ethanol

反应条件

后处理

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

实验过程

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.

来源