Acetic Acid → N-{1-[4-(Methanesulfonyl)phenyl]-2-nitroethylidene}hydroxylamine

HRID 1958440Notes

Reaction equation

HRID 1958440 reaction equation
[CH3:1][S:2]([C:5]1[CH:10]=[CH:9][C:8]([C:11](=O)[CH2:12][N+:13]([O-:15])=[O:14])=[CH:7][CH:6]=1)(=[O:4])=[O:3].[NH2:17][OH:18].Cl.C(O)(=O)C>C(O)C>[CH3:1][S:2]([C:5]1[CH:10]=[CH:9][C:8]([C:11](=[N:17][OH:18])[CH2:12][N+:13]([O-:15])=[O:14])=[CH:7][CH:6]=1)(=[O:4])=[O:3]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 443297Hydroxyamine hydrochlorideHCID 218977141-[4-(Methanesulfonyl)phenyl]-2-nitroethan-1-one

Product 1

HCID 53630456N-{1-[4-(Methanesulfonyl)phenyl]-2-nitroethylidene}hydroxylamine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 1-(4-methanesulfonyl-phenyl)-2-nitro-ethanone (12.5 g, 51.4 mmol) in ethanol (100 mL), was added NH2OH.HCl (3.57 g, 51.4 mmol) and acetic acid (33 mL) at room temperature. The reaction was refluxed for 3 h and cooled to room temperature. The reaction was concentrated under vacuum and extracted with ethyl acetate (200 mL). The reaction was concentrated to afford the crude compound which was recrystallized from petroleum ether/hexane (1/3) as white crystals (10.3 g, 83.4%). 1H NMR (400 Mz, DMSO-d6) δ 12.81 (s, 1H), 8.03 (m, 4H), 5.93 (s, 2H), 3.28 (s, 3H). LCMS 259.2 [M+H].

Workup

  1. temperatureThe reaction was refluxed for 3 h
  2. concentrationThe reaction was concentrated under vacuum
  3. extractionextracted with ethyl acetate (200 mL)
  4. concentrationThe reaction was concentrated

Sources & evidence

ORD record
ord-5969ceb27a7f48769d96ccca7eadb3e2
Source dataset
uspto-grants-2013_04
Patent number
US08410119B2

Reaction notes

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