Methylamine → Cimetidine

HRID 1834563Notes

Reaction equation

HRID 1834563 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)methyl-thio)ethyl]guanidine (8.6 g.), m.p. 141°-143°.

Workup

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

Sources & evidence

ORD record
ord-de113aa829714cb790f3199950755eae
Source dataset
uspto-grants-1978_01
Patent number
US04070475

Reaction notes

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