Dimethylformamide → Cimetidine

HRID 27480Notes

Reaction equation

HRID 27480 reaction equation
[N:1]#[C:2][NH2:3].[Pb].[CH3:5][NH:6][C:7]([NH:9][CH2:10][CH2:11][S:12][CH2:13][C:14]1[NH:18][CH:17]=[N:16][C:15]=1[CH3:19])=S.CN(C)C=O>C(#N)C>[C:2]([NH:3][C:7]([NH:6][CH3:5])=[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:1]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 22262466CH2N2PbHCID 178486120HCID 178486120, compound

Product 1

HCID 178485005Cimetidine

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Lead cyanamide (3.0 g.) was added to a solution of N-methyl-N'-[2-((4-methyl-5-imidazolyl)methylthio)-ethyl]thiourea (2.44 g.) in acetonitrile (50 ml.). Dimethylformamide (b 20 ml.) was added subsequently and the suspension was heated under reflux, with stirring, for 24 hours. Filtration, followed by concentration under reduced pressure and purification of the product by chromatography on a column of silica gel with acetonitrile as eluant and recrystallisation from the same solvent afforded N-cyano-N'-methyl-N"-[2-((4-methyl-5-imidazolyl)- methylthio)ethyl]guanidine, m.p. 139°-141°. (Found: C, 47.3; H, 6.6; N, 33.4; S, 12.6. C10N16N6S requires: C, 47.6; H, 6.4; N, 33.3; S, 12.7).

Workup

  1. temperaturethe suspension was heated
  2. temperatureunder reflux
  3. filtrationFiltration
  4. concentrationfollowed by concentration under reduced pressure and purification of the product by chromatography on a column of silica gel with acetonitrile as eluant
  5. customrecrystallisation from the same solvent

Sources & evidence

ORD record
ord-82666c22d68e4f35aa3ad4bbfc77a705
Source dataset
uspto-grants-1980_09
Patent number
US04221802

Reaction notes

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