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

HRID 441807

Reaction equation

HRID 441807 reaction equation
[CH3:1][N:2]1[CH2:6][CH2:5][N:4]=[C:3]1SC.[N+:9]([CH2:12][C:13]([O:15]C)=[O:14])([O-:11])=[O:10]>[Cl-].[Zn+2].[Cl-]>[CH3:1][N:2]1[CH2:6][CH2:5][NH:4][C:3]1=[C:12]([N+:9]([O-:11])=[O:10])[C:13]([OH:15])=[O:14]

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 3007855ZincchlorideCatalyst

Procedure

19.5 g of 1A, 17.8 g of methyl nitroacetate and a small amount of zinc chloride were mixed and the mixture heated to 100°-105°. After 30 minutes, the solid reaction mixture was washed with ether, then with hot methanol. The mixture then was filtered to give the methyl ester of (1-methyl-2-imidazolidinylidene)nitroacetic acid (1B) as a tan solid, m.p.: 209°-210°.

Workup

  1. temperaturethe mixture heated to 100°-105°
  2. customthe solid reaction mixture
  3. washwas washed with ether
  4. filtrationThe mixture then was filtered

Sources & evidence

ORD record
ord-ba0adfc77e6f49f09f87e2968a44bf0d
Source dataset
uspto-grants-1977_08
Patent number
US04042696

Linked notes

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