Methylamine → Cimetidine

HRID 2072038Notes

Reaction equation

HRID 2072038 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-a8315a6429e0466f8caf952498637203
Source dataset
uspto-grants-1977_09
Patent number
US04049672

Reaction notes

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