Ethanolamine → N-Cyano-N'-(2-hydroxyethyl)-N"-[2-((4-methyl-5-imidazolyl)-methylthio)ethyl]guanidine

HRID 866419Notes

Reaction equation

HRID 866419 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]([CH2:20][NH2:21])[OH:19]>C(O)C>[C:1]([NH:3][C:4]([NH:21][CH2:20][CH2:18][OH:19])=[N:7][CH2:8][CH2:9][S:10][CH2:11][C:12]1[NH:16][CH:15]=[N:14][C:13]=1[CH3:17])#[N:2]

Participants

4

Reactant 2

HCID 700EthanolamineHCID 178503877HCID 178503877, compound

Product 1

HCID 178433310N-Cyano-N'-(2-hydroxyethyl)-N"-[2-((4-methyl-5-imidazolyl)-methylthio)ethyl]guanidine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of N-cyano-N'-[2-((4-methyl-5-imidazolyl)methylthio)ethyl]-S-methylisothiourea (2.7 g) (British Specification No. 1397436) and ethanolamine (1.34 g) in ethanol (50 ml) was heated under reflux for 19 hours. Concentration followed by chromatographic purification on a column of silica gel with chlorofrom-methanol (10:1) as eluant and final recrystallisation from isopropyl alcohol -- acetonitrile gave the title compound, m.p. 146°-7°. (Found: C, 46.8; H, 6.5; N, 29.6; S, 11.2% C11H18N6OS requires: C, 46.8; H, 6.4; N, 29.8; S, 11.4%).

Workup

  1. temperatureunder reflux for 19 hours
  2. concentrationConcentration
  3. customfollowed by chromatographic purification on a column of silica gel with chlorofrom-methanol (10:1) as eluant
  4. customfinal recrystallisation from isopropyl alcohol

Sources & evidence

ORD record
ord-d8495b2c06a5452e8e836c7a951360d1
Source dataset
uspto-grants-1978_07
Patent number
US04098898

Reaction notes

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