Acetic Anhydride → 2-(benzenesulfonyl)-3-ethoxyprop-2-enenitrile

HRID 1077684Notes

Reaction equation

HRID 1077684 reaction equation
[C:1]1([S:7]([CH2:10][C:11]#[N:12])(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH:13](OCC)(OCC)[O:14][CH2:15][CH3:16].C(OC(=O)C)(=O)C.C(OCC)(=O)C>CO>[CH2:15]([O:14][CH:13]=[C:10]([S:7]([C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1)(=[O:8])=[O:9])[C:11]#[N:12])[CH3:16]

Participants

6

Reactant 4

HCID 7918Acetic AnhydrideHCID 8857Ethyl AcetateHCID 31214Ethyl orthoformateHCID 82077Phenylsulphonylacetonitrile

Product 1

HCID 51775592-(benzenesulfonyl)-3-ethoxyprop-2-enenitrileYield 78%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of (phenylsulfonyl)acetonitrile (10.5 g, 0.089 mol) in triethyl orthoformate (21 mL, 0.14 mol) and acetic anhydride (21 mL, 0.2 mol) was heated at 160° C. with removal of ethyl acetate (35 mL). The dark oily residue was dissolved in methanol (60 mL) and the solution was concentrated and recrystallized from hexanes/ethyl acetate to yield (11.98 g, 78%) of the desired product.

Workup

  1. concentrationthe solution was concentrated
  2. customrecrystallized from hexanes/ethyl acetate

Sources & evidence

ORD record
ord-89762a37df2941d59d2cc293b7d3df3f
Source dataset
uspto-grants-1996_08
Patent number
US05545515

Reaction notes

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