Réaction #2487413

Équation de réaction

Diethyldithiocarbamic acid

sodium

4-Chloromethylbenzoic acid

carbamic acid

→

1-((diethylcarbamothioylthio)methyl)benzoic Acid

Rendement 62.0%

Solvants

ethanol

ethanol

Conditions de réaction

Traitement

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

Mode opératoire

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.

Source