Hydrogen Sulfide → 3-amino-N,N-dimethyl-3-thioxopropanamide
Reaction equation
[CH3:1][N:2]([CH3:8])[C:3](=[O:7])[CH2:4][C:5]#[N:6].[SH2:9]>C(N(CC)CC)C>[NH2:6][C:5](=[S:9])[CH2:4][C:3]([N:2]([CH3:8])[CH3:1])=[O:7]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 55 °C
Procedure
A reaction mixture was prepared from 22.4 g. of N,N-dimethylcyanoacetamide, 21 ml. of liquid hydrogen sulfide and 1 ml. of triethylamine. The reaction mixture was placed in an autoclave and the autoclave shaken at about 55° C. for about 12 hours. The reaction mixture was taken from the autoclave and the volatile constituents removed by evaporation. Ethanol was added to the residue, thus producing a crystalline solid. The solid was filtered and the filter cake washed with cold ethanol. Twenty-one grams of 3-amino-3-thioxo-N,N-dimethylpropanamide were obtained melting at 111°-114° C. The compound had the following nmr (CDCl3 +DMSOd6):δ3.07 (doublet, 6H); 3.82 (singlet, 2H); 9.1 (very broad, 1H).
Workup
- customA reaction mixture was prepared from 22.4 g
- customthe volatile constituents removed by evaporation
- additionEthanol was added to the residue
- customthus producing a crystalline solid
- filtrationThe solid was filtered
- washthe filter cake washed with cold ethanol
Sources & evidence
- ORD record
- ord-92bbd982283a4134830e172fca60ac6b
- Source dataset
- uspto-grants-1984_08
- Patent number
- US04468399
Reaction notes
Loading…