Methylamine → Cimetidine

HRID 1577174Notes

Reaction equation

HRID 1577174 reaction equation
[CH3:1][NH2:2].[C:3]([NH:5][C:6](=[N:9][CH2:10][CH2:11][S:12][CH2:13][C:14]1[NH:18][CH:17]=[N:16][C:15]=1[CH3:19])SC)#[N:4]>C(O)C>[C:3]([NH:5][C:6]([NH:2][CH3:1])=[N:9][CH2:10][CH2:11][S:12][CH2:13][C:14]1[NH:18][CH:17]=[N:16][C:15]=1[CH3:19])#[N:4]

Participants

4

Reactant 2

HCID 6329MethylamineHCID 178503877HCID 178503877, compound

Product 1

HCID 178485005Cimetidine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

A solution of methylamine in ethanol (33%, 75 ml.) was added to a solution of N-cyano-N'-[2-((4-methyl-5-imidazolyl)methylthio)ethyl]-S-methylisothiourea (10.1 g.) in ethanol (30 ml.). The reaction mixture was set aside at room temperature for 2.5 hours. Following concentration under reduced pressure, the residue was recrystallised twice from isopropyl alcohol/petroleum ether, affording N-cyano-N'-methyl-N"-[2-((4-methyl-5-imidazolyl)methylthio)ethyl]guanidine (8.6 g.), m.p. 141°-143°. (Found: C, 47.5; H, 6.3; N, 33.2; S, 12.9. C10H16N6S requires: C, 47.6; H, 6.4; N, 33.3; S, 12.7).

Workup

  1. concentrationconcentration under reduced pressure
  2. customthe residue was recrystallised twice from isopropyl alcohol/petroleum ether

Sources & evidence

ORD record
ord-b1dea4e9ff974e22a6f8ef0aed0eed0c
Source dataset
uspto-grants-1981_09
Patent number
US04287198

Reaction notes

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