Methylamine → Cimetidine

HRID 1605285Notes

Reaction equation

HRID 1605285 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 recrystallized 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. C10H16N 6S requires: C, 47.6; H, 6.4; N, 33.3; S, 12.7).

Workup

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

Sources & evidence

ORD record
ord-112b51cf2f13489e8f6b14284d964851
Source dataset
uspto-grants-1976_04
Patent number
US03950333

Reaction notes

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