Acetyl chloride → HCID 53829930, compound

HRID 2260401Notes

Reaction equation

HRID 2260401 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][C@@H:12]2[CH2:17][CH2:16][CH2:15][CH2:14][C@H:13]2[C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)(=[O:10])=[O:9])=[CH:4][CH:3]=1.[C:24](Cl)(=[O:26])[CH3:25].[Cl-].[Al+3].[Cl-].[Cl-]>ClCCl>[C:24]([C:21]1[CH:20]=[CH:19][C:18]([C@@H:13]2[CH2:14][CH2:15][CH2:16][CH2:17][C@H:12]2[NH:11][S:8]([C:5]2[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=2)(=[O:10])=[O:9])=[CH:23][CH:22]=1)(=[O:26])[CH3:25]

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 6451240Aluminum(III) ChlorideHCID 54269428HCID 54269428, compound

Product 1

HCID 53829930HCID 53829930, compoundYield 42.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture maintained at 0° C. of 4.0 g (12 mmoles) of trans-4-chloro-N-(2-phenylcyclohexyl)-benzenesulfonamide (prepared according to Das P. C. et al., Indian J. Chem. (1974), 12, 1139-40), 80 ml of anhydrous dichloromethane and 2.4 g (31 mmoles) of acetyl chloride, 5.3 g (40 mmoles) of aluminum chloride are added by fractions. After 4 hours at 0° C., the reaction mixture is thrown onto an ice-HCl mixture before being extracted with dichloromethane. The organic phase is washed with water to neutrality, dried over Na2SO4 and concentrated. The residue is purified by chromatography on a column of silica (eluant: hexane-ethyl acetate 4/1) to give 2 g of a colorless oil (yield: 42.5%).

Workup

  1. additionare added by fractions
  2. extractionbefore being extracted with dichloromethane
  3. washThe organic phase is washed with water to neutrality
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated
  6. customThe residue is purified by chromatography on a column of silica (eluant: hexane-ethyl acetate 4/1)

Sources & evidence

ORD record
ord-2c86db44fede457fbb0dac8bb5b1deaf
Source dataset
uspto-grants-1995_12
Patent number
US05476846

Reaction notes

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