Water → 4-(Methylsulfonyl)benzonitrile

HRID 901900

Reaction equation

HRID 901900 reaction equation
[OH:1]OS([O-])=O.[K+].[CH3:7][S:8][C:9]1[CH:16]=[CH:15][C:12]([C:13]#[N:14])=[CH:11][CH:10]=1.[OH2:17]>CO>[CH3:7][S:8]([C:9]1[CH:16]=[CH:15][C:12]([C:13]#[N:14])=[CH:11][CH:10]=1)(=[O:1])=[O:17]

Participants

5

Reactant 3

HCID 962Water2×HCID 5909604-(Methylthio)benzonitrileHCID 23707502Potassium hydroxy sulfite

Product 1

HCID 5199814-(Methylsulfonyl)benzonitrile

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of oxone (18.42 g, 0.03 mol) in water (70 ml) was added dropwise to the vigorous stirred solution of 4-methylthiobenzonitrile (1.49 g, 0.01 mol) in methanol (50 ml) at 20° C. and stirring was continued for three hours. The reaction mixture was diluted with water (50 ml) and extracted with ethyl acetate. The ethyl acetate extract was washed with water, dried over anhydrous sodium sulphate and concentrated under reduced pressure to finish the title compound (1.3 g, 72.2%), mp 145-149° C. The compound was used with out any purification for the next step. 1H-NMR (CDCl3):δ 3.1 (s, 3H), 7.8-7.9 (d, 2H), 8.08-8.1 (d, 2H).

Workup

  1. extractionextracted with ethyl acetate
  2. extractionThe ethyl acetate extract
  3. washwas washed with water
  4. dry with materialdried over anhydrous sodium sulphate
  5. concentrationconcentrated under reduced pressure
  6. customThe compound was used with out any purification for the next step

Sources & evidence

ORD record
ord-e49c99a73935496d9b326a44e8837331
Source dataset
uspto-grants-2008_04
Patent number
US07365069B2

Linked notes

Loading…