Acetyl chloride → HCID 53829930, compound

HRID 274115Notes

Reaction equation

HRID 274115 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-91a4a224a3da4126a17703b9b6562336
Source dataset
uspto-grants-1995_02
Patent number
US05387709

Reaction notes

Loading…