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

HRID 1864168Notes

Reaction equation

HRID 1864168 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 (400Mz, 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-5b96463bc08b43cda12a969ea085a3e5
Source dataset
uspto-grants-2009_12
Patent number
US07625906B2

Reaction notes

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