Methylamine → Cimetidine

HRID 1648817Notes

Reaction equation

HRID 1648817 reaction equation
[CH3:1][NH2:2].[C:3]([NH:5][C:6](=[N:10][CH2:11][CH2:12][S:13][CH2:14][C:15]1[NH:19][CH:18]=[N:17][C:16]=1[CH3:20])OCC)#[N:4]>C(O)C.O>[C:3]([NH:5][C:6]([NH:2][CH3:1])=[N:10][CH2:11][CH2:12][S:13][CH2:14][C:15]1[NH:19][CH:18]=[N:17][C:16]=1[CH3:20])#[N:4]

Participants

5

Reactant 2

HCID 6329MethylamineHCID 178468270HCID 178468270, compound

Product 1

HCID 178485005CimetidineYield 75%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

90 ml of a 30% aqueous solution of monomethylamine is added dropwise with cooling by ice to 4.3 g of N-cyano-N'-[2-((4-methyl-5-imidazolyl)methylthio)ethyl]-O-ethylisourea dissolved in the mixture of 90 ml of ethanol and 60 ml of water. After reaction at 0° C. overnight, the solution is concentrated under reduced pressure and chromatographed similarly as in Example 1 (iii) to separate a reaction solution. Thus obtained solution is concentrated under reduced pressure and is crystallized from isopropyl alcohol-ether to yield 3.0 g of cimetidine, namely N-cyano-N'-methyl-N"-[2-((4-methyl-5-imidazolyl)methylthio)ethyl]guanidine (yield: 75.0%)

Workup

  1. customAfter reaction at 0° C. overnight
  2. concentrationthe solution is concentrated under reduced pressure
  3. customto separate a reaction solution
  4. concentrationThus obtained solution is concentrated under reduced pressure
  5. customis crystallized from isopropyl alcohol-ether

Sources & evidence

ORD record
ord-dee67ae02aa34405b26203f1e2f83aaa
Source dataset
uspto-grants-1983_11
Patent number
US04413129

Reaction notes

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