AcOH AcOAc → N-[3-Cyano-4-(ethanesulfonyl)phenyl]acetamide

HRID 1667587Notes

Reaction equation

HRID 1667587 reaction equation
[CH2:1]([S:3]([C:6]1[CH:13]=[CH:12][C:11]([N+:14]([O-])=O)=[CH:10][C:7]=1[C:8]#[N:9])(=[O:5])=[O:4])[CH3:2].[C:17](O)(=[O:19])[CH3:18].C(OC(=O)C)(=O)C>[Fe]>[C:8]([C:7]1[CH:10]=[C:11]([NH:14][C:17](=[O:19])[CH3:18])[CH:12]=[CH:13][C:6]=1[S:3]([CH2:1][CH3:2])(=[O:5])=[O:4])#[N:9]

Participants

4

Reactant 2

HCID 21895370AcOH AcOAcHCID 574481822-(Ethanesulfonyl)-5-nitrobenzonitrile

Product 1

HCID 57448183N-[3-Cyano-4-(ethanesulfonyl)phenyl]acetamideYield 83%

Reagents, catalysts & solvents 1

HCID 23925IronCatalyst

Conditions

Temperature
100 °C

Procedure

To 5B (3.60 g, 15.0 mmol) in 1:1 acetic acid/acetic anhydride (150 mL), Fe (4.20 g, 75.2 mmol) was added. The reaction mixture was heated to 100° C. for 2 h then poured into ice. After the ice melted, the product was extracted with ethyl acetate, and the organic layer was washed with saturated aqueous NaHCO3 and brine. The organic layer was dried (Na2SO4), filtered and concentrated to provide 5C (3.14 g, 83%). LC-MS: 241.18 (M+H)+.

Workup

  1. additionthen poured into ice
  2. extractionthe product was extracted with ethyl acetate
  3. washthe organic layer was washed with saturated aqueous NaHCO3 and brine
  4. dry with materialThe organic layer was dried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-0cbc4430504741bbaca3cef9e5e9c921
Source dataset
uspto-grants-2011_10
Patent number
US08044242B2

Reaction notes

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