Dimethyl N-cyanodithioiminocarbonate → Carbamimidothioic acid, N-cyano-N'-2-propynyl-, methyl ester

HRID 1395378Notes

Reaction equation

HRID 1395378 reaction equation
[C:1]([N:3]=[C:4](SC)[S:5][CH3:6])#[N:2].[CH2:9]([NH2:12])[C:10]#[CH:11]>C(#N)C>[C:1]([NH:3][C:4](=[N:12][CH2:9][C:10]#[CH:11])[S:5][CH3:6])#[N:2]

Participants

4

Reactant 2

HCID 66289Dimethyl N-cyanodithioiminocarbonateHCID 239041Propargylamine

Product 1

HCID 2805748Carbamimidothioic acid, N-cyano-N'-2-propynyl-, methyl esterYield 81%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of dimethyl cyanodithioimidocarbonate [prepared according to the procedure described in J. Org. Chem., 32, 1566 (1967)] (16.0 g, 0.109 mole) and propargylamine (6.03 g, 0.109 mole) in acetonitrile (320 ml) was stirred at releux for 4 hours, then at 25° for 12 hours. Workup gave the title compound (13.58 g, 81%), mp 160°-164°.

Sources & evidence

ORD record
ord-3ebf1b9e36294b09b9c732edb06cf310
Source dataset
uspto-grants-1980_05
Patent number
US04203909

Reaction notes

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