Sodium Nitrite → HCID 178504894, compound

HRID 2309576Notes

Reaction equation

HRID 2309576 reaction equation
[Cl:1][CH2:2][C:3](=[O:14])[CH2:4][C:5]([O:7][CH2:8][CH2:9][S:10]([CH3:13])(=[O:12])=[O:11])=[O:6].[N:15]([O-])=[O:16].[Na+]>C(O)(=O)C.O>[Cl:1][CH2:2][C:3](=[O:14])[C:4](=[N:15][OH:16])[C:5]([O:7][CH2:8][CH2:9][S:10]([CH3:13])(=[O:12])=[O:11])=[O:6]

Participants

5

Reactant 2

HCID 23668193Sodium NitriteHCID 543240772-(Methanesulfonyl)ethyl 4-chloro-3-oxobutanoate

Product 1

HCID 178504894HCID 178504894, compoundYield 85%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

In 315 ml of glacial acetic acid was suspended 156.3 g (0.644 mole) of methylsulfonylethyl 4-chloroacetoacetate as obtained in Example 1. The suspension was cooled to 5° C. or below and a solution of 44.4 g (0.644 mole) of sodium nitrite in 140 ml of water was added at 0°-5° C. over a period of about 2 hours. The mixture was stirred for 30 minutes, poured in ice water and extracted with ethyl acetate. The organic layer was washed with water and dried over anhydrous sodium sulfate. The solvent was then distilled off to give 148.7 g of methylsulfonylethyl 4-chloro-2-hydroxyiminoacetoacetate as an oil.

Workup

  1. customas obtained in Example 1
  2. temperatureThe suspension was cooled to 5° C. or below
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with water
  5. dry with materialdried over anhydrous sodium sulfate
  6. distillationThe solvent was then distilled off

Sources & evidence

ORD record
ord-b338687a9ef645b9ba290d76968ed610
Source dataset
uspto-grants-1987_09
Patent number
US04695639

Reaction notes

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