Cyanamide → Metiamide

HRID 372267Notes

Reaction equation

HRID 372267 reaction equation
C(NC(N)=N)#N.[CH3:7][NH:8][C:9]([NH:11][CH2:12][CH2:13][S:14][CH2:15][C:16]1[N:17]=[CH:18][NH:19][C:20]=1[CH3:21])=[S:10].[N:22]#[C:23][NH2:24].N#CN.[Pb]>>[C:23]([NH:24][C:9]([NH:8][CH3:7])=[N:11][CH2:12][CH2:13][S:14][CH2:15][C:16]1[N:17]=[CH:18][NH:19][C:20]=1[CH3:21])#[N:22].[CH3:7][NH:8][C:9]([NH:11][CH2:12][CH2:13][S:14][CH2:15][C:16]1[N:17]=[CH:18][NH:19][C:20]=1[CH3:21])=[S:10]

Participants

6

Reactant 4

HCID 9864CyanamideHCID 1548992MetiamideHCID 22262466CH2N2PbHCID 178418324HCID 178418324, compound

Product 2

HCID 1548992MetiamideHCID 178484998HCID 178484998, compound

Procedure

The compounds of Formula I are also useful as intermediates in the production of cyanoguanidine compounds. For example N-methyl-N'-[2-((5-methyl-4-imidazolyl)methylthio)ethyl]thiourea may be reacted with a heavy metal salt of cyanamide such as lead cyanamide to yield N-cyano-N'-methyl-N"-[2-((5-methyl-4-imidazolyl)methylthio)ethyl]guanidine, or N-methyl-N'-[2-((5-methyl-4-imidazolyl)methylthio)ethyl]thiourea may be alkylated and the resultant isothiourea treated with a strong base and cyanamide to give N-cyano-N'-methyl-N"-[2-((5-methyl-4-imidazolyl)methylthio)ethyl]guanidine.

Sources & evidence

ORD record
ord-73004e662a0e46d1a2d05c86b223ee06
Source dataset
uspto-grants-1978_05
Patent number
US04090026

Reaction notes

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