Toluene → HCID 68291332, compound

HRID 339821Notes

Reaction equation

HRID 339821 reaction equation
COC1C=C(OC)C=CC=1C[NH:6][S:7]([CH:10]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[C:11]([OH:14])([CH3:13])[CH3:12])(=[O:9])=[O:8].FC(F)(F)C(O)=O.C1(C)C=CC=CC=1>ClCCl>[OH:14][C:11]([CH3:13])([CH3:12])[CH:10]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[S:7]([NH2:6])(=[O:8])=[O:9]

Participants

5

Reactant 3

HCID 1140TolueneHCID 6422Trifluoroacetic acidHCID 68291892HCID 68291892, compound

Product 1

HCID 68291332HCID 68291332, compoundYield 55.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 2.67 g of N-(2,4-dimethoxybenzyl)-2-hydroxy-2-methyl-1-phenylpropane-1-sulfonamide in 20 ml of dichloromethane was admixed with 3.74 ml of trifluoroacetic acid and stirred at room temperature for 2 hours. The starting solution was coevaporated twice with 100 ml of toluene and the crude product was purified using by means of normal phase chromatography using a Flashmaster with an n-heptane/ethyl acetate gradient. The product-containing fractions were combined and concentrated by rotary evaporation. This gave the product (0.90 g) with a molecular weight of 229.3 g/mol (C10H15NO3S).

Workup

  1. customthe crude product was purified
  2. concentrationconcentrated by rotary evaporation

Sources & evidence

ORD record
ord-d815130885694f99a23dcb1323e74e8a
Source dataset
uspto-grants-2014_11
Patent number
US08895547B2

Reaction notes

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