Water → 1-(3-Bromophenyl)-2-hydroxy-2-methylpropane-1-sulfonamide

HRID 339836Notes

Reaction equation

HRID 339836 reaction equation
COC1C=C(OC)C=CC=1C[NH:6][S:7]([CH:10]([C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([Br:21])[CH:16]=1)[C:11]([OH:14])([CH3:13])[CH3:12])(=[O:9])=[O:8].FC(F)(F)C(O)=O.O.C(=O)([O-])O.[Na+]>ClCCl>[Br:21][C:17]1[CH:16]=[C:15]([CH:10]([S:7]([NH2:6])(=[O:8])=[O:9])[C:11]([OH:14])([CH3:12])[CH3:13])[CH:20]=[CH:19][CH:18]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6422Trifluoroacetic acidHCID 516892Sodium BicarbonateHCID 68291617N-(2,4-Dimethoxybenzyl)-1-(3-bromophenyl)-2-hydroxy-2-methylpropane-1-sulfonamide

Product 1

HCID 682918601-(3-Bromophenyl)-2-hydroxy-2-methylpropane-1-sulfonamideYield 70.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 8.63 g of N-[2,4-dimethoxybenzyl]-1-(3-bromophenyl)-2-hydroxy-2-methylpropane-1-sulfonamide in 40 ml of dichloromethane was admixed with 10 ml of trifluoroacetic acid and stirred at room temperature for 30 minutes. The reaction solution was admixed with 40 ml of water, and gradually and cautiously with 150 ml of a saturated aqueous sodium hydrogencarbonate solution. The precipitate was filtered off with suction, washed with water and dried over P2O5 under reduced pressure. The crude product was purified by means of normal phase chromatography using a Flashmaster with a dichloromethane/methanol gradient. The product-containing fractions were combined and concentrated by rotary evaporation. This gave the product (4.11 g) with a molecular weight of 308.2 g/mol (C10H14BrNO3S); MS (ESI): m/e=325 (M+H2O+H+).

Workup

  1. filtrationThe precipitate was filtered off with suction
  2. washwashed with water
  3. dry with materialdried over P2O5 under reduced pressure
  4. customThe crude product was purified by means of normal phase chromatography
  5. concentrationconcentrated by rotary evaporation

Sources & evidence

ORD record
ord-905a95438271452d9c55378432525c8a
Source dataset
uspto-grants-2014_11
Patent number
US08895547B2

Reaction notes

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