CH2N2Pb → HCID 178433311, compound

HRID 2058229Notes

Reaction equation

HRID 2058229 reaction equation
[N:1]#[C:2][NH2:3].[Pb].[CH3:5][C:6]1[N:7]=[CH:8][NH:9][C:10]=1[CH2:11][S:12][CH2:13][CH2:14][NH:15][C:16]([NH:18][CH2:19][CH2:20][S:21][CH2:22][C:23]1[NH:27][CH:26]=[N:25][C:24]=1[CH3:28])=S>C(#N)C.CN(C)C=O>[C:2]([NH:3][C:16]([NH:15][CH2:14][CH2:13][S:12][CH2:11][C:10]1[NH:9][CH:8]=[N:7][C:6]=1[CH3:5])=[N:18][CH2:19][CH2:20][S:21][CH2:22][C:23]1[NH:27][CH:26]=[N:25][C:24]=1[CH3:28])#[N:1]

Participants

5

Reactant 2

HCID 22262466CH2N2Pb2×HCID 178433325HCID 178433325, compound

Product 1

HCID 178433311HCID 178433311, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6342AcetonitrileSolvent

Procedure

Lead cyanamide (8.7 g.) was added to a solution of N,N'-bis-[2-((4-methyl-5-imidazolyl)methylthio)ethyl]thiourea in acetonitrile (100 ml.) and dimethyl formamide (20 ml.) and the resultant suspension was heated under reflux with stirring for 24 hours. Additional lead cyanamide (8.7 g.) was added and heating was continued for hours. Following filtration and concentration, the residue was chromatographed on a column of silica gel, eluting with ethyl acetate-isopropyl alcohol (5:1). Recrystallization from isopropyl alcohol-isopropyl acetate afforded N-cyano-N',N"-bis-[2-((4-methyl-5-imidazolyl) methylthio)ethyl]guanidine (0.6 g.), m.p. 92°-95°.

Workup

  1. temperatureunder reflux
  2. temperatureheating
  3. waitwas continued for hours
  4. filtrationfiltration and concentration
  5. customthe residue was chromatographed on a column of silica gel
  6. washeluting with ethyl acetate-isopropyl alcohol (5:1)
  7. customRecrystallization from isopropyl alcohol-isopropyl acetate

Sources & evidence

ORD record
ord-7fa02947b9d74ac787ba2233dee1ee6a
Source dataset
uspto-grants-1980_07
Patent number
US04215125

Reaction notes

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