Sodium Chloride → benzhydryl 4-bromo-2-hydroxyimino-3-oxobutanoate

HRID 444558Notes

Reaction equation

HRID 444558 reaction equation
[Br:1][CH2:2][C:3](=[O:21])[CH2:4][C:5]([O:7][CH:8]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)=[O:6].[N:22]([O-])=[O:23].[Na+].[Cl-].[Na+]>C(O)(=O)C.O>[Br:1][CH2:2][C:3](=[O:21])[C:4](=[N:22][OH:23])[C:5]([O:7][CH:8]([C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1)[C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1)=[O:6]

Participants

6

Reactant 3

HCID 5234Sodium ChlorideHCID 15080911Benzhydryl 4-bromo-3-oxobutyrateHCID 23668193Sodium Nitrite

Product 1

HCID 178520135benzhydryl 4-bromo-2-hydroxyimino-3-oxobutanoate

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

In 30 ml of acetic acid there were dissolved 6.94 g of benzhydryl 4-bromo-3-oxobutyrate and, under ice-cooling and stirring, a solution of 1.588 g of sodium nitrite in 6 ml of water was added dropwise. The mixture was further stirred at that temperature for 20 minutes and, following addition of 60 ml of a saturated aqueous solution of sodium chloride, the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with a saturated aqueous solution of sodium chloride and dried over magnesium sulfate. The solvent was removed under reduced pressure to recover 7.56 g of the captioned compound.

Workup

  1. temperatureunder ice-cooling
  2. stirringThe mixture was further stirred at that temperature for 20 minutes
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe ethyl acetate layer was washed with a saturated aqueous solution of sodium chloride
  5. dry with materialdried over magnesium sulfate
  6. customThe solvent was removed under reduced pressure
  7. customto recover 7.56 g of the captioned compound

Sources & evidence

ORD record
ord-3500744ec0a54d4c8c1eb290e28f6661
Source dataset
uspto-grants-1981_04
Patent number
US04264595

Reaction notes

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