Dichloromethane → N-[3-(bromoacetyl)phenyl]hexadecane-1-sulfonamide

HRID 444302Notes

Reaction equation

HRID 444302 reaction equation
[Br:1]Br.[CH2:3]([S:19]([NH:22][C:23]1[CH:24]=[C:25]([C:29](=[O:31])[CH3:30])[CH:26]=[CH:27][CH:28]=1)(=[O:21])=[O:20])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18].C(Cl)Cl>C(O)(=O)C>[CH2:3]([S:19]([NH:22][C:23]1[CH:24]=[C:25]([C:29](=[O:31])[CH2:30][Br:1])[CH:26]=[CH:27][CH:28]=1)(=[O:20])=[O:21])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18]

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 24408Bromine2×HCID 23464850N-(3-acetylphenyl)hexadecane-1-sulfonamide

Product 1

HCID 23464849N-[3-(bromoacetyl)phenyl]hexadecane-1-sulfonamide

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Bromine, 4.72 g (1.52 ml) was added to 25 g (0.059 M) of the product of Step A in 75 ml of glacial acetic acid at 70° C. Decolorization of bromine was instant. The reaction was followed by thin layer chromatography (CH2Cl2, silica gel) until the starting material was practically absent. The solid precipitated on cooling was collected by filtration, recrystallized from hexane to give 23.5 g of product (about 80% based on m-aminoacetophenone): mp 92°-5° C. Mass spectrum showed some dibrominated material.

Workup

  1. customThe solid precipitated
  2. temperatureon cooling
  3. filtrationwas collected by filtration
  4. customrecrystallized from hexane
  5. customto give 23.5 g of product (about 80% based on m-aminoacetophenone)

Sources & evidence

ORD record
ord-5c490608efa447e289077b6f3a52aadf
Source dataset
uspto-grants-1981_04
Patent number
US04263393

Reaction notes

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