Hydrochloric Acid → 2-benzoyl-4-bromo-N-(4-methanesulfonylbenzyl)-N-(2-oxopentyl)benzamide

HRID 750361Notes

Reaction equation

HRID 750361 reaction equation
[C:1]([C:9]1[CH:34]=[C:33]([Br:35])[CH:32]=[CH:31][C:10]=1[C:11]([N:13]([CH2:25][CH:26]([OH:30])[CH2:27][CH2:28][CH3:29])[CH2:14][C:15]1[CH:20]=[CH:19][C:18]([S:21]([CH3:24])(=[O:23])=[O:22])=[CH:17][CH:16]=1)=[O:12])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.O.Cl>CS(C)=O>[C:1]([C:9]1[CH:34]=[C:33]([Br:35])[CH:32]=[CH:31][C:10]=1[C:11]([N:13]([CH2:14][C:15]1[CH:16]=[CH:17][C:18]([S:21]([CH3:24])(=[O:22])=[O:23])=[CH:19][CH:20]=1)[CH2:25][C:26](=[O:30])[CH2:27][CH2:28][CH3:29])=[O:12])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 8471TriethylamineHCID 230607862-benzoyl-4-bromo-N-(2-hydroxypentyl)-N-(4-methanesulfonylbenzyl)benzamide

Product 1

HCID 230608192-benzoyl-4-bromo-N-(4-methanesulfonylbenzyl)-N-(2-oxopentyl)benzamideYield 81.8%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

[Step 2] To a solution of 2-benzoyl-4-bromo-N-(2-hydroxypentyl)-N-(4-methanesulfonylbenzyl)benzamide (2.7 g) in DMSO (27 ml) was added triethylamine (11 ml), and pyridine sulfur trioxide complex (6.2 g) was added to the mixture at room temperature. The mixture was stirred for 1 hr. and added to water. 10% Hydrochloric acid was added to acidify the aqueous layer and the mixture was extracted with ethyl acetate. The organic layer was washed with water, saturated aqueous sodium hydrogen carbonate, water and saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure to give 2-benzoyl-4-bromo-N-(4-methanesulfonylbenzyl)-N-(2-oxopentyl)benzamide (2.2 g).

Workup

  1. additionwas added to the mixture at room temperature
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe organic layer was washed with water, saturated aqueous sodium hydrogen carbonate, water and saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-239edc06f2ef4dfba4c32b4d04da959c
Source dataset
uspto-grants-2008_07
Patent number
US07402595B2

Reaction notes

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