Ammonia → Ethyl 2-carbamoyl-2-(cyclopropyloxyimino)acetate

HRID 1074339Notes

Reaction equation

HRID 1074339 reaction equation
[CH:1]1([O:4][N:5]=[C:6]([C:12]([OH:14])=O)[C:7]([O:9][CH2:10][CH3:11])=[O:8])[CH2:3][CH2:2]1.P(Cl)(Cl)(Cl)=O.[NH3:20].C(=O)(O)[O-].[Na+]>O1CCCC1.C(OCC)(=O)C.CN(C)C=O>[C:12]([C:6](=[N:5][O:4][CH:1]1[CH2:3][CH2:2]1)[C:7]([O:9][CH2:10][CH3:11])=[O:8])(=[O:14])[NH2:20]

Participants

8

Reactant 4

HCID 222AmmoniaHCID 24813Phosphorus oxychlorideHCID 516892Sodium BicarbonateHCID 54136521Ethyl hydrogen alpha-(cyclopropyloxyimino)malonate

Product 1

HCID 54332569Ethyl 2-carbamoyl-2-(cyclopropyloxyimino)acetate

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

An activated acid, prepared from ethyl hydrogen α-(cyclopropyloxyimino)malonate (syn isomer)(19.78 g), phosphorus oxychloride (11.9 ml) and N,N-dimethylformamide (9.91 ml) by a conventional manner, was added to a saturated ammonia solution in tetrahydrofuran at -30° C. The mixture was gently warmed to ambient temperature. The mixture was poured into a mixture of ethyl acetate (1 l) and ice-water (1 l) and adjusted to pH 7 with saturated aqueous solution of sodium bicarbonate. The organic layer was separated washed with saturated aqueous solution of sodium chloride, dried over magnesium sulfate and concentrated in vacuo. The residue was subjected to column chromatography on silica gel (200 g) using chloroform as an eluent to give ethyl 2-carbamoyl-2-(cyclopropyloxyimino)acetate (syn isomer) as a crystal (10.51 g).

Workup

  1. customThe organic layer was separated
  2. washwashed with saturated aqueous solution of sodium chloride
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-c55138e435294b2bb1e55d81df14f102
Source dataset
uspto-grants-1990_11
Patent number
US04973699

Reaction notes

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