Dimethylformamide → HCID 178433314, compound

HRID 2072037Notes

Reaction equation

HRID 2072037 reaction equation
[N:1]#CN.[Pb].C[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>[CH3:19][C:15]1[N:16]=[CH:17][NH:18][C:14]=1[CH2:13][S:12][CH2:11][CH2:10][NH:9][C:7]([NH2:1])=[NH:6]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 22262466CH2N2PbHCID 178486120HCID 178486120, compound

Product 1

HCID 178433314HCID 178433314, compound

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 (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; N, 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-20b602c0a61b4d4191bded53969427a8
Source dataset
uspto-grants-1977_09
Patent number
US04049672

Reaction notes

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