Propargylamine → HCID 178457562, compound

HRID 544347Notes

Reaction equation

HRID 544347 reaction equation
[C:1]([NH:3][C:4](=[N:7][CH2:8][CH2:9][S:10][CH2:11][C:12]1[NH:16][CH:15]=[N:14][C:13]=1[CH3:17])SC)#[N:2].[CH2:18]([NH2:21])[C:19]#[CH:20]>CO>[C:1]([NH:3][C:4]([NH:7][CH2:8][CH2:9][S:10][CH2:11][C:12]1[NH:16][CH:15]=[N:14][C:13]=1[CH3:17])=[N:21][CH2:18][C:19]#[CH:20])#[N:2]

Participants

4

Reactant 2

HCID 239041PropargylamineHCID 178503877HCID 178503877, compound

Product 1

HCID 178457562HCID 178457562, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The mixture of N-cyano-N'-{2-[(4-methyl-5-imidazolyl)methylthio]ethyl}-S-methylisothiourea (10.0 g; 0.0371 mole) and distilled propargylamine (20 ml; 0.325 mole) in methanol (50 ml) was stirred at reflux, under a positive pressure nitrogen atmosphere (nitrogen sweep), for 20.5 hours. The solvent and excess amine were then removed by evaporation to leave a yellow-brown oil that readily crystallized. Trituration of the crude product under isopropanol (30 ml) gave the title compound as an off-white, friable solid (8.11 g, 79%); m.p. 146°-148.5°.

Workup

  1. temperatureat reflux, under a positive pressure nitrogen atmosphere (nitrogen sweep), for 20.5 hours
  2. customThe solvent and excess amine were then removed by evaporation
  3. customto leave a yellow-brown oil that
  4. customreadily crystallized

Sources & evidence

ORD record
ord-132b748d7aef4ec485160d1612417e0c
Source dataset
uspto-grants-1984_05
Patent number
USRE031588

Reaction notes

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