Urea → HCID 53672254, compound

HRID 1906598Notes

Reaction equation

HRID 1906598 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-860cd3d8eb9c45e5baf9bc75fe83f8f7
Source dataset
uspto-grants-1987_03
Patent number
US04652651

Reaction notes

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