n-methylhydrazinecarboxamide → 1-[(Z)-[amino-(1-methyl-5-nitroimidazol-2-yl)methylidene]amino]-1-ethylurea

HRID 2398997Notes

Reaction equation

HRID 2398997 reaction equation
[CH2:1]([N:3]([C:5]([NH2:7])=[O:6])[NH2:4])[CH3:2].[CH3:8][NH:9][C:10](=[O:13])[NH:11][NH2:12].[CH3:14][N:15]1[C:19]([N+:20]([O-:22])=[O:21])=[CH:18][N:17]=[C:16]1[C:23](=[NH:27])OCC>>[CH3:14][N:15]1[C:19]([N+:20]([O-:22])=[O:21])=[CH:18][N:17]=[C:16]1[C:23]([NH:4][N:3]([CH2:1][CH3:2])[C:5]([NH2:7])=[O:6])=[NH:27].[CH3:14][N:15]1[C:19]([N+:20]([O-:22])=[O:21])=[CH:18][N:17]=[C:16]1[C:23]([NH:12][NH:11][C:10]([NH:9][CH3:8])=[O:13])=[NH:27]

Participants

5

Reactant 3

HCID 256005n-methylhydrazinecarboxamideHCID 21432269Ethyl 1-methyl-5-nitro-1H-imidazole-2-carboximidateHCID 214322711-Ethylhydrazinecarboxamide

Product 2

HCID 1784656201-[(Z)-[amino-(1-methyl-5-nitroimidazol-2-yl)methylidene]amino]-1-ethylureaHCID 1784859491-[(Z)-[amino-(1-methyl-5-nitroimidazol-2-yl)methylidene]amino]-3-methylurea

Procedure

In a similar manner, 2-ethylsemicarbazide and 4-methylsemicarbazide are reacted with ethyl 1-methyl-5-nitro-2-imidazolecarboximidate to give 1-(1-methyl-5-nitro-2-imidazolecarboximidoyl)-2-ethylsemicarbazide (IIIG) and 1-(1-methyl-5-nitro-2-imidazolecarboximidoyl)-4-methylsemicarbazide (IIIH), respectively.

Sources & evidence

ORD record
ord-809b12ec645842f8bd2c404d57638c93
Source dataset
uspto-grants-1977_05
Patent number
US04026903

Reaction notes

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