Water → HCID 18953985, compound

HRID 1491661Notes

Reaction equation

HRID 1491661 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([NH:10][C:11](=[O:20])[CH:12]=[C:13](N2CCCC2)[CH3:14])=[CH:6][CH:5]=1)([O-:3])=[O:2].[CH3:21][CH2:22][O:23][C:24](/[C:26](/Cl)=[N:27]\[OH:28])=[O:25].O>ClCCl>[CH3:14][C:13]1[O:28][N:27]=[C:26]([C:24]([O:23][CH2:22][CH3:21])=[O:25])[C:12]=1[C:11](=[O:20])[NH:10][C:7]1[CH:8]=[CH:9][C:4]([N+:1]([O-:3])=[O:2])=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 962WaterHCID 6399471Ethyl 2-chloro-2-(hydroxyimino)acetateHCID 57221882HCID 57221882, compound

Product 1

HCID 18953985HCID 18953985, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

A suspension of 12.38 g (45 mmol) of the crude N-(4-nitrophenyl)-3-pyrrolidyl-2-butenamide in 200 ml of dry dichloromethane was cooled to 0° C. and 7.50 g (49.5 mmol) of ethyl chlorooximidoacetate were added in one portion. The reaction mixture was stirred at -5° C. to 0° C. for 2 hours and was then poured into 200 ml of water. The aqueous layer was extracted with 100 ml of dichloromethane and the combined organic extract was washed with 100 ml of 10% HCl, 5% NaHCO3 solution and then dried over MgSO4. Evaporation of the solvent gave 10.91 g (76%) of ethyl 5-methyl-4-[N-(4-nitrophenyl)]carbamoyl-3-isoxazolecarboxylate as a white crystalline solid melting at 151°-53° C. (from ethyl acetate);

Workup

  1. extractionThe aqueous layer was extracted with 100 ml of dichloromethane
  2. extractionthe combined organic extract
  3. washwas washed with 100 ml of 10% HCl, 5% NaHCO3 solution
  4. dry with materialdried over MgSO4
  5. customEvaporation of the solvent

Sources & evidence

ORD record
ord-15a8eff56bc4427a80da18003e7b4d94
Source dataset
uspto-grants-1994_12
Patent number
US05371099

Reaction notes

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