1-Cyano-2,3-dimethylisothiourea → Cimetidine

HRID 27478Notes

Reaction equation

HRID 27478 reaction equation
[CH3:1][C:2]1[N:3]=[CH:4][NH:5][C:6]=1[CH2:7][S:8][CH2:9][CH2:10][NH2:11].[C:12]([NH:14][C:15](=[N:18][CH3:19])SC)#[N:13]>C(#N)C>[C:12]([NH:14][C:15]([NH:18][CH3:19])=[N:11][CH2:10][CH2:9][S:8][CH2:7][C:6]1[NH:5][CH:4]=[N:3][C:2]=1[CH3:1])#[N:13]

Participants

4

Reactant 2

HCID 1111031-Cyano-2,3-dimethylisothioureaHCID 178433288HCID 178433288, compound

Product 1

HCID 178485005Cimetidine

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of 4-methyl-5-[(2-aminoethyl)thiomethyl]-imidazole (17.0 g.) and N-cyano-N',S-dimethylisothiourea (11.2 g.) in acetonitrile (500 ml.) was heated under reflux for 24 hours. Following concentration, the reside was chromatographed on a column of silica gel with acetonitrile as eluant and the product obtained was finally recrystallised from acetonitrile-ether to yield N-cyano-N'-methyl-N"-[2-((4-methyl-5-imidazolyl)methylthio)ethyl) guanidine, m.p. 141°-2°. (Found: C, 47.2; H, 6.4; N, 33.4; S, 12.4. C10H16N6S requires: C, 47.6; H, 6.4; N, 33.3; S, 12.7).

Workup

  1. temperatureunder reflux for 24 hours
  2. concentrationconcentration
  3. customthe reside was chromatographed on a column of silica gel with acetonitrile as eluant
  4. customthe product obtained
  5. customwas finally recrystallised from acetonitrile-ether

Sources & evidence

ORD record
ord-31fda24a02fb4941afafe5d6c53f8547
Source dataset
uspto-grants-1980_09
Patent number
US04221802

Reaction notes

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