Water → 3-Methanesulfonyl-2-(2,4,6-trimethylphenyl)acrylonitrile

HRID 1383304

Reaction equation

HRID 1383304 reaction equation
O[CH:2]=[C:3]([C:6]1[C:11]([CH3:12])=[CH:10][C:9]([CH3:13])=[CH:8][C:7]=1[CH3:14])[C:4]#[N:5].[CH3:15][S:16](Cl)(=[O:18])=[O:17].O>N1C=CC=CC=1>[CH3:15][S:16]([CH:2]=[C:3]([C:6]1[C:11]([CH3:12])=[CH:10][C:9]([CH3:13])=[CH:8][C:7]=1[CH3:14])[C:4]#[N:5])(=[O:18])=[O:17]

Participants

5

Reactant 3

HCID 962WaterHCID 31297Methanesulfonyl chlorideHCID 701428183-Hydroxy-2-(2,4,6-trimethylphenyl)acrylonitrile

Product 1

HCID 536820093-Methanesulfonyl-2-(2,4,6-trimethylphenyl)acrylonitrileYield 105.1%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A solution of intermediate 1 (1 g) in 10 ml pyridine was cooled to 0° C. under nitrogen and then treated with methanesulfonyl chloride (0.67 g) with good stirring. The solution was allowed to come to room temperature and stirred for 1 hour. The reaction mixture was poured into water and extracted with ethyl acetate. The organic phase was washed with 1M HCl, water and brine, dried (MgSO4) and concentrated to give 3-methanesulfonyl-2-(2,4,6-trimethylphenyl)acrylonitrile (intermediate 2) as a brown solid (1.4 g).

Workup

  1. customto come to room temperature
  2. extractionextracted with ethyl acetate
  3. washThe organic phase was washed with 1M HCl, water and brine
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-af568a6e2a924fa6b7619dfae69a4515
Source dataset
uspto-grants-2001_07
Patent number
US06255310B1

Linked notes

Loading…