Reaktion #2487413

Reaktionsgleichung

Diethyldithiocarbamic acid

sodium

4-Chloromethylbenzoic acid

carbamic acid

→

1-((diethylcarbamothioylthio)methyl)benzoic Acid

Ausbeute 62.0%

Lösungsmittel

ethanol

ethanol

Reaktionsbedingungen

Aufarbeitung

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

Vorschrift

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.

Quelle