CH2N2Pb → HCID 178433311, compound

HRID 2398677Notes

Reaction equation

HRID 2398677 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 24 hours. Following filtration and concentration, the residue was chromatographed on a column of silica gel, eluting with ethyl acetate-isopropyl alcohol (5:1). Recrystallisation 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 24 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. customRecrystallisation from isopropyl alcohol-isopropyl acetate

Sources & evidence

ORD record
ord-4c40cb25a9114d04b6d2cf7003599357
Source dataset
uspto-grants-1977_05
Patent number
US04025527

Reaction notes

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