Urea → HCID 53672254, compound

HRID 1709365Notes

Reaction equation

HRID 1709365 reaction equation
[CH3:1][O:2][N:3]=[C:4]([C:10]([CH2:12]Br)=O)[C:5]([O:7][CH2:8][CH3:9])=[O:6].[NH2:14][C:15]([NH2:17])=[O:16]>CN(C)C=O>[NH2:17][C:15]1[O:16][CH:12]=[C:10]([C:4](=[N:3][O:2][CH3:1])[C:5]([O:7][CH2:8][CH3:9])=[O:6])[N:14]=1

Participants

4

Reactant 2

HCID 1176UreaHCID 54053279Butanoic acid, 4-bromo-2-(methoxyimino)-3-oxo-, ethyl ester

Product 1

HCID 53672254HCID 53672254, compoundYield 26%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 50.4 g (0.2 mol) of ethyl 2-methoxyimino-4-bromoacetoacetate [M. Ochiai et al., Chem. Pharm. Bull. 25, 3115 (1977)] and 60.1 g (1 mol) of urea in 200 ml of dimethylformamide is heated to 100° C. for 30 minutes. Thereafter, the mixture is evaporated, the residue is taken up in 800 ml of water, neutralized with sodium bicarbonate and extracted with ethyl acetate. The ethyl acetate extract is chromatographed on silica gel with acetonitrile/methylene chloride (1:1). There is obtained ethyl 2-(2-amino-4-oxazolyl)-2-methoxyimino-acetate in a yield of 26%; melting point 120° C. (decomposition).

Workup

  1. customThereafter, the mixture is evaporated
  2. extractionextracted with ethyl acetate
  3. extractionThe ethyl acetate extract
  4. customis chromatographed on silica gel with acetonitrile/methylene chloride (1:1)

Sources & evidence

ORD record
ord-afc0fb38e9054f7094b14a1537db24ce
Source dataset
uspto-grants-1990_08
Patent number
US04948898

Reaction notes

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