p-Toluenesulfonic acid → N-{5-[2-(4-bromophenyl)ethyl]-2,2-dimethyl-1,3-dioxan-5-yl}acetamide

HRID 1641527Notes

Reaction equation

HRID 1641527 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][C:10]([NH:15][C:16](=[O:18])[CH3:17])([CH2:13][OH:14])[CH2:11][OH:12])=[CH:4][CH:3]=1.CO[C:21](OC)([CH3:23])[CH3:22].C1(C)C=CC(S(O)(=O)=O)=CC=1>CC(C)=O>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][C:10]2([NH:15][C:16](=[O:18])[CH3:17])[CH2:11][O:12][C:21]([CH3:23])([CH3:22])[O:14][CH2:13]2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 64952,2-DimethoxypropaneHCID 57624600N-[3-(4-bromophenyl)-1,1-bis(hydroxymethyl)propyl]acetamide

Product 1

HCID 46202882N-{5-[2-(4-bromophenyl)ethyl]-2,2-dimethyl-1,3-dioxan-5-yl}acetamideYield 87.3%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A solution of N-[3-(4-bromophenyl)-1,1-bis(hydroxymethyl)propyl]acetamide (42.2 g) of Reference Example 4, acetone dimethyl acetal (41.9 g) and a catalytic amount of p-toluenesulfonic acid in acetone (200 mL) was stirred at room temperature for one day. The reaction mixture was concentrated under reduced pressure, and the residual crude crystals were suspended in aqueous sodium hydrogen carbonate solution and collected by filtration to give the title compound (41.5 g) as white crystals.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. filtrationcollected by filtration

Sources & evidence

ORD record
ord-e73c4946036b4ed8a8cde575bbf2c225
Source dataset
uspto-grants-2012_02
Patent number
US08114902B2

Reaction notes

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