반응 #2487413

반응 방정식

Diethyldithiocarbamic acid

sodium

4-Chloromethylbenzoic acid

carbamic acid

→

1-((diethylcarbamothioylthio)methyl)benzoic Acid

수율 62.0%

용매

ethanol

ethanol

반응 조건

후처리

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

실험 절차

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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