Hydrochloric Acid → N-[2,2,2-Trifluoro-1-(4-methoxyphenyl)ethylidene]hydroxylamine

HRID 1636024Notes

Reaction equation

HRID 1636024 reaction equation
[F:1][C:2]([F:20])([F:19])[C:3]([C:6]1[CH:11]=[CH:10][C:9]([O:12][C:13]2C=CC=CC=2)=[CH:8][CH:7]=1)=[N:4][OH:5].Cl>C(Cl)Cl>[F:1][C:2]([F:19])([F:20])[C:3]([C:6]1[CH:11]=[CH:10][C:9]([O:12][CH3:13])=[CH:8][CH:7]=1)=[N:4][OH:5]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 591151932,2,2-Trifluoro-1-(4-phenoxyphenyl)-ethanone oxime

Product 1

HCID 59115151N-[2,2,2-Trifluoro-1-(4-methoxyphenyl)ethylidene]hydroxylamineYield 122.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

35 g (124 mmol) of 2,2,2-trifluoro-1-(4-phenoxyphenyl)-ethanone oxime (mixture of E- and Z-isomers) prepared according to the method described in example 80.1 is dissolved in 300 ml of methylene chloride. To the solution is added 1.1 ml of conc. HCl and stirred at room temperature for 4.5 hours. The reaction mixture is washed with water and brine, dried over MgSO4, and concentrated, yielding 33.4 g of 2,2,2-trifluoro-1-(4-methoxyphenyl)-ethanone oxime (single isomer) as a white solid. The structure is confirmed by the 1H-NMR spectrum (CDCl3). δ [ppm]: 7.00-7.12 (m, 4H), 7.19 (t, 1H), 7.39 (t, 2H), 7.57 (d, 2H), 8.95 (s, 1H).

Workup

  1. washThe reaction mixture is washed with water and brine
  2. dry with materialdried over MgSO4
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-81dcdb31491b46ffb1a20f09575ba1aa
Source dataset
uspto-grants-2003_01
Patent number
US06512020B1

Reaction notes

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