Potassium Carbonate → HCID 18320645, compound

HRID 1699448Notes

Reaction equation

HRID 1699448 reaction equation
[Cl:1][C:2]1[C:7]2[C:8]([CH3:14])([CH3:13])[NH:9][S:10](=[O:12])(=[O:11])[C:6]=2[CH:5]=[CH:4][CH:3]=1.[CH2:15]([O:17][CH:18]([O:21][CH2:22][CH3:23])[CH2:19]Br)[CH3:16].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[CH2:15]([O:17][CH:18]([O:21][CH2:22][CH3:23])[CH2:19][N:9]1[C:8]([CH3:14])([CH3:13])[C:7]2[C:2]([Cl:1])=[CH:3][CH:4]=[CH:5][C:6]=2[S:10]1(=[O:12])=[O:11])[CH3:16]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 74852Ethane, 2-bromo-1,1-diethoxy-HCID 18320637HCID 18320637, compound

Product 1

HCID 18320645HCID 18320645, compoundYield 65.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
120 °C

Procedure

7.7 g (33 mmol) of 4-chloro-3,3-dimethyl-2,3-dihydro-1,2-benzoisothiazole 1,1-dioxide, 8.25 ml (55 mmol) of bromoacetaldehyde diethyl acetal and 7.0 g of potassium carbonate were taken up in 100 ml of dry DMF and stirred at 120° C. for 5 h. The reaction mixture was poured into ice-water and then extracted with ethyl acetate, and the organic phase was washed with water and dried over sodium sulfate. The solvent was removed under reduced pressure, the crude product was purified by column chromatography. 7.5 g (65%) of the product were obtained as an oil in this way.

Workup

  1. extractionextracted with ethyl acetate
  2. washthe organic phase was washed with water
  3. dry with materialdried over sodium sulfate
  4. customThe solvent was removed under reduced pressure
  5. customthe crude product was purified by column chromatography

Sources & evidence

ORD record
ord-ec12768166f949659066b9ceabab9339
Source dataset
uspto-grants-2002_02
Patent number
US06346622B1

Reaction notes

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