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

HRID 750364
Notes
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Reaction equation

HRID 750364 reaction equation
[C:1]([C:9]1[CH:35]=[C:34]([Br:36])[CH:33]=[CH:32][C:10]=1[C:11]([N:13]([CH2:25][CH:26]([OH:31])[CH2:27][CH2:28][CH2:29][CH3:30])[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:35]=[C:34]([Br:36])[CH:33]=[CH:32][C:10]=1[C:11]([N:13]([CH2:14][C:15]1[CH:16]=[CH:17][C:18]([S:21]([CH3:24])(=[O:23])=[O:22])=[CH:19][CH:20]=1)[CH2:25][C:26](=[O:31])[CH2:27][CH2:28][CH2:29][CH3:30])=[O:12])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 8471TriethylamineHCID 230606192-benzoyl-4-bromo-N-(2-hydroxyhexyl)-N-(4-methanesulfonylbenzyl)benzamide

Product 1

HCID 230606932-benzoyl-4-bromo-N-(4-methanesulfonylbenzyl)-N-(2-oxohexyl)benzamideYield 76.4%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

[Step 2] To a solution (25 ml) of 2-benzoyl-4-bromo-N-(2-hydroxyhexyl)-N-(4-methanesulfonylbenzyl)benzamide (2.3 g) in DMSO was added triethylamine (9 ml), and pyridine sulfur trioxide complex (5.2 g) was added 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-oxohexyl)benzamide (1.75 g).

Workup

  1. additionwas added 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-09264dbb8c84469c9e021b2b0f3e0461
Source dataset
uspto-grants-2008_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07402595B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes