Formic Acid → HCID 54488460, compound

HRID 255733Notes

Reaction equation

HRID 255733 reaction equation
[Br:1][CH2:2][CH2:3][O:4][N:5]=[C:6]([C:12](=[O:14])[CH3:13])[C:7]([O:9][CH2:10][CH3:11])=[O:8].S(Cl)([Cl:18])(=O)=O.C(O)=O>O>[Br:1][CH2:2][CH2:3][O:4][N:5]=[C:6]([C:12](=[O:14])[CH2:13][Cl:18])[C:7]([O:9][CH2:10][CH3:11])=[O:8]

Participants

5

Reactant 3

HCID 284Formic AcidHCID 24648Sulfuryl chlorideHCID 53922552HCID 53922552, compound

Product 1

HCID 54488460HCID 54488460, compoundYield 82.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
40 °C

Procedure

A mixture of ethyl 2-(2-bromoethoxyimino)-3-oxobutyrate (syn isomer, 168 g.), sulfuryl chloride (87.3 g.) and formic acid (168 ml.) was stirred at 40° C. for 10 minutes and at room temperature for 5.5 hours. After adding water (1 l.) to the resultant solution, the mixture was extracted with methylene chloride. The extract was washed with water, a saturated aqueous solution of sodium bicarbonate and a saturated aqueous solution of sodium chloride in turn, dried over magnesium sulfate, and then concentrated in vacuo to give ethyl 2-(2-bromoethoxyimino)-4-chloro-3-oxobutyrate (syn isomer, 156 g.), oil.

Workup

  1. extractionthe mixture was extracted with methylene chloride
  2. washThe extract was washed with water
  3. dry with materiala saturated aqueous solution of sodium bicarbonate and a saturated aqueous solution of sodium chloride in turn, dried over magnesium sulfate
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-d8d9b3f8f26c4ab2949ed4665d1c3b8e
Source dataset
uspto-grants-1987_10
Patent number
US04698337

Reaction notes

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