Methyl 2-nitroacetate → (1-Methyl-2-imidazolidinylidene)nitroacetic acid

HRID 972829

Reaction equation

HRID 972829 reaction equation
[N+:1]([CH2:4][C:5]([O:7]C)=[O:6])([O-:3])=[O:2].[CH3:9][N:10]1[CH2:14][CH2:13][N:12]=[C:11]1SC>C(O)(C)C>[CH3:9][N:10]1[CH2:14][CH2:13][NH:12][C:11]1=[C:4]([N+:1]([O-:3])=[O:2])[C:5]([OH:7])=[O:6]

Participants

4

Reactant 2

HCID 17206Methyl 2-nitroacetateHCID 103968741-methyl-2-methylsulfanyl-4,5-dihydro-1H-imidazole

Product 1

HCID 86735005(1-Methyl-2-imidazolidinylidene)nitroacetic acid

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

35.7 g methyl nitroacetate was added slowly to a refluxing mixture of 39.0 g of 1A and 300 ml of isopropyl alcohol. The mixture then was refluxed for 1 hour with provision to remove the methyl mercaptan by-product. The mixture was cooled and filtered to give the methyl ester of (1-methyl-2-imidazolidinylidene)nitroacetic acid (1B) as a solid, m.p.: 214°-217° (with decomposition).

Workup

  1. temperatureThe mixture then was refluxed for 1 hour with provision
  2. customto remove the methyl mercaptan by-product
  3. temperatureThe mixture was cooled
  4. filtrationfiltered

Sources & evidence

ORD record
ord-e80e326091fc446892471a59408ec401
Source dataset
uspto-grants-1977_10
Patent number
US04053619

Linked notes

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