Cyanamide → Metiamide

HRID 838856Notes

Reaction equation

HRID 838856 reaction equation
[S].[CH3:2][NH:3][C:4]([NH:6][CH2:7][CH2:8][S:9][CH2:10][C:11]1[N:12]=[CH:13][NH:14][C:15]=1[CH3:16])=[S:5].[N:17]#[C:18][NH2:19]>[Hg].N#CN.[Cd]>[C:18]([NH:19][C:4]([NH:3][CH3:2])=[N:6][CH2:7][CH2:8][S:9][CH2:10][C:11]1[N:12]=[CH:13][NH:14][C:15]=1[CH3:16])#[N:17].[CH3:2][NH:3][C:4]([NH:6][CH2:7][CH2:8][S:9][CH2:10][C:11]1[N:12]=[CH:13][NH:14][C:15]=1[CH3:16])=[S:5]

Participants

7

Reactant 3

HCID 9864CyanamideHCID 1548992MetiamideHCID 5362487Sulfur

Product 2

HCID 1548992MetiamideHCID 178484998HCID 178484998, compound

Reagents, catalysts & solvents 2

HCID 23931MercuryCatalystHCID 86734572Cadmium;cyanamideCatalyst

Procedure

The compounds of Formula I wherein E is sulphur are also useful as intermediates for the production of compounds of Formula I wherein E is NCN, 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, mercury or cadmium 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 product reacted with cyanamide and a suitable strong base such as potassium t-butoxide to yield N-cyano-N'-methyl-N"-[2-((5-methyl-4-imidazolyl)methylthio)ethyl]guanidine.

Sources & evidence

ORD record
ord-4c19c59ecfe4439c8037529d0db53078
Source dataset
uspto-grants-1978_06
Patent number
US04093621

Reaction notes

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