Sulfuryl chloride → 4-Chloro-2-(n-propoxyimino)acetoacetic acid methyl ester
Reaction equation
[CH3:1][O:2][C:3](=[O:13])[C:4](=[N:8][O:9][CH2:10][CH2:11][CH3:12])[C:5]([CH3:7])=[O:6].S(Cl)([Cl:17])(=O)=O>C(O)(=O)C>[CH3:1][O:2][C:3](=[O:13])[C:4](=[N:8][O:9][CH2:10][CH2:11][CH3:12])[C:5]([CH2:7][Cl:17])=[O:6]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 40 °C
Procedure
To a solution of 7.4 g of 2-(n-propoxyimino)acetoacetic acid methyl ester in 7.4 ml of acetic acid is added 5.5 g of sulfuryl chloride, and the mixture is stirred for 10 minutes at 40° C., then for 6 hours at room temperature. The reaction solution is poured into 100 ml of ice-water, and subjected to extraction twice with chloroform. The extract is washed with an aqueous solution of sodium chloride, and aqueous solution of sodium bicarbonate and water in this order, and dried over anhydrous sodium sulfate. The solvent is evaporated under reduced pressure to yield 8.2 g (94%) of 4-chloro-2-(n-propoxyimino)acetoacetic acid methyl ester as a pale yellow oily product.
Workup
- waitfor 6 hours at room temperature
- extractionsubjected to extraction twice with chloroform
- washThe extract is washed with an aqueous solution of sodium chloride, and aqueous solution of sodium bicarbonate and water in this order
- dry with materialdried over anhydrous sodium sulfate
- customThe solvent is evaporated under reduced pressure
Sources & evidence
- ORD record
- ord-f6b029045bcc40c4b32bb3d465790223
- Source dataset
- uspto-grants-1988_11
- Patent number
- US04782147
Reaction notes
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