Water → N-benzhydryl-4-(bromomethyl)benzenesulfonamide

HRID 40790

Reaction equation

HRID 40790 reaction equation
[CH:1]([NH2:14])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.[Br:22][CH2:23][C:24]1[CH:29]=[CH:28][C:27]([S:30](Cl)(=[O:32])=[O:31])=[CH:26][CH:25]=1.O>ClCCl>[CH:1]([NH:14][S:30]([C:27]1[CH:26]=[CH:25][C:24]([CH2:23][Br:22])=[CH:29][CH:28]=1)(=[O:31])=[O:32])([C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7036BenzhydrylamineHCID 8471TriethylamineHCID 27344094-(Bromomethyl)benzenesulfonyl chloride

Product 1

HCID 67021864N-benzhydryl-4-(bromomethyl)benzenesulfonamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Benzhydrylamine (640 μL) was dissolved in dichloromethane (5.0 mL). To the solution, triethylamine (645 μl) and 4-(bromomethyl)benzenesulfonyl chloride (1.0 g) were added at 0° C., and the mixture was stirred at room temperature for 2 hours. To the reaction mixture, water (10 mL) was added, and the resultant mixture was then extracted with chloroform (30 mL). The organic layer was washed with brine (15 mL), dried over anhydrous sodium sulfate, and then concentrated under reduced pressure. The residue was purified by silica gel column chromatography (40% ethyl acetate/hexane) to obtain the title compound (753 mg).

Workup

  1. extractionthe resultant mixture was then extracted with chloroform (30 mL)
  2. washThe organic layer was washed with brine (15 mL)
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (40% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-39757e3b8a604a86b768458e01915af5
Source dataset
uspto-grants-2013_09
Patent number
US08530490B2

Linked notes

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