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

HRID 236851Notes

Reaction equation

HRID 236851 reaction equation
[CH3:1][S:2][C:3](SC)=[N:4][C:5]#[N:6].[CH2:9]([NH2:12])[C:10]#[CH:11]>C(#N)C>[C:5]([NH:4][C:3](=[N:12][CH2:9][C:10]#[CH:11])[S:2][CH3:1])#[N:6]

Participants

4

Reactant 2

HCID 66289Dimethyl N-cyanodithioiminocarbonateHCID 239041Propargylamine

Product 1

HCID 2805748Carbamimidothioic acid, N-cyano-N'-2-propynyl-, methyl esterYield 81.3%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of dimethyl cyanodithioiminocarbonate (16.00 g, 0.109 mole) and propargylamine (6.03 g, 0.109 mole) in acetonitrile (320 ml) was stirred at reflux for 4 hours, and then at 25° for 12 hours. The mixture was cooled and filtered to yield the title compound (13.58 g, 81%), mp 160°-164°.

Workup

  1. temperatureat reflux for 4 hours
  2. temperatureThe mixture was cooled
  3. filtrationfiltered

Sources & evidence

ORD record
ord-8bd3b5f6a9ed4c1fb76890970039a41a
Source dataset
uspto-grants-1979_06
Patent number
US04158013

Reaction notes

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