Ammonium dithiocarbamate

Yellow crystals. Soluble in water.

General procedure: Following literature procedures, 1 ammonia gas was bubbled into carbon disulfide 1 (16.7g, 0.22 mol) in THF (100 ml) keeping the temperature below 45 °C. After 1 hr, the reaction was stopped by allowing the temperature to decrease to rt. The excess ammonia gas was removed by streaming N2 for 30 min or by rotary evaporation under vacuum. The precipitate was collected by filtration to afford white solid ammonium dithiocarbamate 2 (23.1 g, 96percent). Methyl iodide (17.8 g, 0.125 mol) was added to a solution of 2 (5.5 g, 0.05 mol) in acetone (100 ml) at rt and the mixture was stirred for 24 hr. The solid was collected by filtration, washed with chilled acetone (20 ml) and dried under vacuum to provide white solid S, S’-dimethyliminodithiocarbonate hydroiodide ammonium iodide 3 (18.9 g, 96percent). 3 (7.9 g, 0.02 mol) was treated with sat. aq. NaHCO3 solution (100 ml x 2) and the organic products extracted with dichloromethane (50 ml). The organic layer was dried over Na2SO4 and concentrated in vacuo to a clear, colorless liquid 4 (2.3 g, 95percent). 1H NMR (400 MHz, CDCl3) δ 8.88 (s, 1H), 2.42 (s, 6H). 13C NMR (101 MHz, CDCl3) δ 172.10, 14.50. HRMS (ESI+) m/z calcd for C3H8N+ 122.0098, found 122.0096.Carbon disulfide 100 mL (1.6 mole) was added to a three-necked flask, and the temperature was lowered to -5 DEG C. 300 mL of a 15percent ammonia-ethanol solution was added dropwise, and the mixture was continuously stirred at -5 DEG C. for 4 hours.The mixture was filtered with suction, washed with ether and dried to obtain 152 g of ammonium dithiocarbamate in a yellow crystal. The yield was 86percent.

Instead of H2S or (NH4)2S for pptg metals in chemical analysis; synthesis of heterocyclic compounds.

(1977) AT LEAST 4.54X10+5 GRAMS|(1981) No Data

Molecular Weight:110.21
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:2
Exact Mass:109.99724055
Monoisotopic Mass:109.99724055
Topological Polar Surface Area:60.1
Heavy Atom Count:5
Complexity:27.5
Covalently-Bonded Unit Count:2
Compound Is Canonicalized:Yes