Methylamine → Cimetidine

HRID 2397684Notes

Reaction equation

HRID 2397684 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].[CH3:12][NH2:13]>C(O)C>[C:12]([NH:5][C:4]([NH:3][CH3:2])=[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 6329MethylamineHCID 178433288HCID 178433288, compound

Product 1

HCID 178485005Cimetidine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 4-methyl-5-[(2-aminoethyl)thiomethyl]imidazole (1.93 g.) and dimethyl-N-cyanoimidodithiocarbonate (1.65 g.) in ethanol (33 ml.) was set aside overnight at room temperature. Ethanolic methylamine (33%, 22 ml.) was added and the solution was then set aside for 4 hours. Concentration and recrystallisation from isopropyl alcohol-ether yielded N-cyano-N'-methyl-N"-[2-((4-methyl-5-imidazolyl)methylthio)ethyl]guanidine (2.0 g.), m.p. 139°-140°. (Found: C, 47.5; H, 6.5; N, 33.3; S, 12.7. C10H16N6S requires: C, 47.6; H, 6.4; N, 33.3; S, 12.7).

Workup

  1. concentrationConcentration and recrystallisation from isopropyl alcohol-ether

Sources & evidence

ORD record
ord-b4e90c91895c4920924281c6f9cc56a3
Source dataset
uspto-grants-1977_05
Patent number
US04022797

Reaction notes

Loading…