Acetyl chloride → HCID 18921491, compound

HRID 1654957Notes

Reaction equation

HRID 1654957 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][CH2:12][CH:13]2[CH2:21][C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[CH2:14]2)(=[O:10])=[O:9])=[CH:4][CH:3]=1.[Cl-].[Al+3].[Cl-].[Cl-].[C:26](Cl)(=[O:28])[CH3:27]>C(Cl)Cl>[C:26]([C:17]1[CH:16]=[C:15]2[C:20](=[CH:19][CH:18]=1)[CH2:21][CH:13]([CH2:12][NH:11][S:8]([C:5]1[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=1)(=[O:10])=[O:9])[CH2:14]2)(=[O:28])[CH3:27]

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 6451240Aluminum(III) ChlorideHCID 189215132-[(4-Chlorophenyl)sulfonylaminomethyl)indan

Product 1

HCID 18921491HCID 18921491, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

369 mg (1.15 mmol) of 2-[(4-chlorophenyl)sulfonylaminomethyl)indan was dissolved in 5 ml of methylene chloride, to which were added 460 mg (4.20 mmol) of anhydrous aluminum chloride under ice-cooling and then 302 mg (3.80 mmol) of acetyl chloride dropwise. After stirring for 30 minutes at the same temperature, the reaction solution was admixed with ice, and the organic phase was washed with water and saturated-aqueous sodium bicarbonate, dried and the solvent was removed. The residue was recrystallized from a solvent mixture of ethyl acetate and isopropylether to obtain 310 mg of colorless crystals. Yield: 75%

Workup

  1. temperaturecooling
  2. washthe organic phase was washed with water and saturated-aqueous sodium bicarbonate
  3. customdried
  4. customthe solvent was removed
  5. customThe residue was recrystallized from a solvent mixture of ethyl acetate and isopropylether

Sources & evidence

ORD record
ord-bb479d3f49d04861aeaf2ae84c133540
Source dataset
uspto-grants-1995_04
Patent number
US05409956

Reaction notes

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