Sodium Bicarbonate → N-Benzyl-N-[2-benzyloxy-5-(2-bromoacetyl)phenyl]methanesulfonamide

HRID 1696840Notes

Reaction equation

HRID 1696840 reaction equation
[Br-:1].[Br-].[Br-].C1([N+](C)(C)C)C=CC=CC=1.C1([N+](C)(C)C)C=CC=CC=1.C1([N+](C)(C)C)C=CC=CC=1.[C:34]([C:37]1[CH:38]=[CH:39][C:40]([O:55][CH2:56][C:57]2[CH:62]=[CH:61][CH:60]=[CH:59][CH:58]=2)=[C:41]([N:43]([CH2:48][C:49]2[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=2)[S:44]([CH3:47])(=[O:46])=[O:45])[CH:42]=1)(=[O:36])[CH3:35].C(=O)(O)[O-].[Na+]>C1COCC1>[CH2:48]([N:43]([C:41]1[CH:42]=[C:37]([C:34](=[O:36])[CH2:35][Br:1])[CH:38]=[CH:39][C:40]=1[O:55][CH2:56][C:57]1[CH:58]=[CH:59][CH:60]=[CH:61][CH:62]=1)[S:44]([CH3:47])(=[O:46])=[O:45])[C:49]1[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=1

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 12363924N-(5-Acetyl-2-benzyloxyphenyl)-N-benzylmethanesulfonamideHCID 17977687Phenyltrimethylammonium bromide dibromide

Product 1

HCID 86607679N-Benzyl-N-[2-benzyloxy-5-(2-bromoacetyl)phenyl]methanesulfonamideYield 85%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Phenyltrimethylammonium tribromide (1.19 g, 3.16 mmol) was added to a solution of N-(5-acetyl-2-benzyloxyphenyl)-N-benzylmethanesulfonamide (32) (1.23 g, 3.01 mmol) in anhydrous THF (15 mL) in three portions. The reaction mixture was stirred at rt for 16 h. An aqueous sodium bicarbonate solution (5%, 15 mL) was then added. The mixture was extracted with dichloromethane and combined organics were concentrated by rotary evaporation. The resulting residue was purified by Biotage silica gel column chromatography eluting with dichloromethane to give bromo ketone 33 as a solid (1.25 g, 85% yield): 1H NMR (500 MHz, CDCl3) δ 2.85 (s, 3H), 4.21 (s, 2H), 4.75 (br, 2H), 5.19 (s, 2H), 7.08 (d, 1H), 7.22 (m, 5H), 7.43 (m, 5H), 7.65 (d, 1H), 7.92 (dd, 1H).

Workup

  1. extractionThe mixture was extracted with dichloromethane
  2. concentrationcombined organics were concentrated by rotary evaporation
  3. customThe resulting residue was purified by Biotage silica gel column chromatography
  4. washeluting with dichloromethane

Sources & evidence

ORD record
ord-9879d8b0080e468983b71eab37cd290a
Source dataset
uspto-grants-2012_04
Patent number
US08163758B2

Reaction notes

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