Propargylamine → N-Cyano-N'-(2-propyn-1-yl)-N"-{2-[(2-pyridyl)methylthio]ethyl}guanidine

HRID 894130Notes

Reaction equation

HRID 894130 reaction equation
[C:1]([NH:3][C:4](=[N:7][CH2:8][CH2:9][S:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][N:13]=1)SC)#[N:2].[CH2:18]([NH2:21])[C:19]#[CH:20]>CO>[C:1]([NH:3][C:4]([NH:21][CH2:18][C:19]#[CH:20])=[N:7][CH2:8][CH2:9][S:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][N:13]=1)#[N:2]

Participants

4

Reactant 2

HCID 239041PropargylamineHCID 12889408N-cyano-N'[2-(2-pyridylmethylthio)ethyl]-S-methylisothiourea

Product 1

HCID 136023173N-Cyano-N'-(2-propyn-1-yl)-N"-{2-[(2-pyridyl)methylthio]ethyl}guanidine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of the product of Step A (4.0 g; 15.0 mmoles) and propargylamine (6.88 g; 125 mmoles) in methanol (20 ml) was stirred and heated to reflux temperature under a positive pressure of nitrogen for 20 hours. The reaction mixture was evaporated under reduced pressure and the product recrystallized from acetonitrile to give the title compound; mp 124.5°-130.5° C. (remelted at 128°-131.5° C.).

Workup

  1. temperatureheated
  2. temperatureto reflux temperature under a positive pressure of nitrogen for 20 hours
  3. customThe reaction mixture was evaporated under reduced pressure
  4. customthe product recrystallized from acetonitrile

Sources & evidence

ORD record
ord-3cc9a929940d49778dc4c1599bfe99f3
Source dataset
uspto-grants-1981_08
Patent number
US04282363

Reaction notes

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