Water → HCID 24704709, compound

HRID 550568Notes

Reaction equation

HRID 550568 reaction equation
[CH3:1][C:2]([C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([NH2:10])[CH:5]=1)=[O:3].N1C=CC=CC=1.[CH2:17]([S:20](Cl)(=[O:22])=[O:21])[CH2:18][CH3:19].O>ClCCl>[C:2]([C:4]1[CH:5]=[C:6]([NH:10][S:20]([CH2:17][CH2:18][CH3:19])(=[O:22])=[O:21])[CH:7]=[CH:8][CH:9]=1)(=[O:3])[CH3:1]

Participants

6

Reactant 4

HCID 962WaterHCID 1049PyridineHCID 74173'-AminoacetophenoneHCID 662791-Propanesulfonyl chloride

Product 1

HCID 24704709HCID 24704709, compoundYield 100.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1 g (7.4 mmol) of 3-aminoacetophenone were dissolved in 35 ml of dry dichloromethane. To the resultant solution cooled at 0° C. 0.89 ml (11.09 mmol) of anhydrous pyridine and 1.26 g (8.87 mmol) of 1-propanesulfonic acid chloride were added. After stirring the reaction mixture for 20 h at room temperature and under inert atmosphere, 15 ml of water were added. The two layers were separated, and the aqueous layer was washed with 2×15 ml of dichloromethane. The organic layers were washed with 30 ml of water and dried over anhydrous sodium sulfate. The dichloromethane layer was evaporated to dryness to yield a yellow solid, 1.8 g (yield=100%) of N-(3-acetylphenyl)-1-propane-sulfonamide which was directly used for the following reaction.

Workup

  1. customThe two layers were separated
  2. washthe aqueous layer was washed with 2×15 ml of dichloromethane
  3. washThe organic layers were washed with 30 ml of water
  4. dry with materialdried over anhydrous sodium sulfate
  5. customThe dichloromethane layer was evaporated to dryness

Sources & evidence

ORD record
ord-076fece14880486fb6b837d51b779443
Source dataset
uspto-grants-2011_05
Patent number
US07947688B2

Reaction notes

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