Dimetridazole → HCID 21827597, compound

HRID 224501Notes

Reaction equation

HRID 224501 reaction equation
[CH3:1][N:2]1[C:6]([N+:7]([O-:9])=[O:8])=[CH:5][N:4]=[C:3]1[CH3:10].[Cl-].[CH2:12]([O:14][C:15](=[O:19])[C:16]([OH:18])=[O:17])[CH3:13].C(N([CH2:25][CH3:26])CC)C>CCOCC>[C:16]([O:18][C:16]([C:15]([O:19][CH2:25][CH3:26])=[O:14])=[CH:10][C:3]1[N:2]([CH3:1])[C:6]([N+:7]([O-:9])=[O:8])=[CH:5][N:4]=1)(=[O:17])[C:15]([O:14][CH2:12][CH3:13])=[O:19]

Participants

5

Reactant 3

HCID 3090DimetridazoleHCID 8471TriethylamineHCID 23618337Oxalic acid monoethylester chloride

Product 1

HCID 21827597HCID 21827597, compoundYield 54%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

The reaction of 1,2-dimethyl-5-nitroimidazole with oxalic acid ethyl ester chloride in the course of 22 hours in the presence of triethylamine and of substantial amounts of ether gives 1-carbethoxy-2-(1-methyl-5-nitro-imidazol-2-yl)-vinyl ethyl oxalate in 54 percent yield; the latter compound, on treatment with ethanol, gives 1-methyl-5-nitro-imidazol-2-yl-pyruvic acid ethyl ester in 43 percent yield (J. Heterocycl., loc. cit., 904 and 905). ##STR4##

Sources & evidence

ORD record
ord-1280b96a4ee24fa8b177e39fe0c1c120
Source dataset
uspto-grants-1980_11
Patent number
US04232165

Reaction notes

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