Methylamine → Cimetidine

HRID 262596Notes

Reaction equation

HRID 262596 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-9ab898b8a3ca4880b2bf7d7085f7fb0d
Source dataset
uspto-grants-1979_05
Patent number
US04154844

Reaction notes

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