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

HRID 1413558Notes

Reaction equation

HRID 1413558 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 85%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of dimethyl cyanodithioimidocarbonate (16.0 g; 0.109 mole) and propargylamine (6.03 g; 0.109 mole) in acetonitrile (320 ml) was stirred at reflux for 4 hours, then at ambient temperature for 12 hours. Workup gave 13.58 g (85%) of N-cyano-N'-(2-propyn-1-yl)-S-methylisothiourea; mp 160°-164°.

Workup

  1. temperatureat reflux for 4 hours

Sources & evidence

ORD record
ord-40f7f5996dc043048c0f7cbdd7c61362
Source dataset
uspto-grants-1981_02
Patent number
US04250316

Reaction notes

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