Dimethylformamide → HCID 178485059, compound

HRID 1605287Notes

Reaction equation

HRID 1605287 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[N:15]=[CH:16][NH:17][CH:18]=1)=S.CN(C)C=O>C(#N)C>[C:2]([NH:3][C:7]([NH:9][CH2:10][CH2:11][S:12][CH2:13][C:14]1[N:15]=[CH:16][NH:17][CH:18]=1)=[N:6][CH3:5])#[N:1]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 22262466CH2N2PbHCID 178486117HCID 178486117, compound

Product 1

HCID 178485059HCID 178485059, compoundYield 31.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Lead cyanamide (24.7 g) was added to a solution of N-methyl-N'-[2-(4-imidazolylmethylthio)ethyl]thiourea (11.5 g.) in acetonitrile (250 ml.) containing dimethylformamide. The stirred suspension was heated under reflux for 48 hours. Filtration followed by concentration under reduced pressure and purification of the product on a column of silica gel with ethyl acetate-isopropyl alcohol (2.1) as eluant gave N-cyano-N'-[2-(4-imidazolylmethylthio)ethyl]-N"-methylguanidine (3.7 g), m.p. 138°-140° (from acetonitrile). (Found: C, 45.7; H, 5.9; N, 35.5; S, 13.5. C9H14N6S requires: C, 45.4; H, 5.9 N, 35.3; S, 13.5).

Workup

  1. temperatureThe stirred suspension was heated
  2. temperatureunder reflux for 48 hours
  3. filtrationFiltration
  4. concentrationfollowed by concentration under reduced pressure and purification of the product on a column of silica gel with ethyl acetate-isopropyl alcohol (2.1) as eluant

Sources & evidence

ORD record
ord-7547e54ec5f748bdb58e68532d173785
Source dataset
uspto-grants-1976_04
Patent number
US03950333

Reaction notes

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