Hydroxylamine HCl → HCID 59115139, compound

HRID 1358159Notes

Reaction equation

HRID 1358159 reaction equation
[F:1][C:2]([F:14])([F:13])[C:3]([C:5]1[CH:10]=[CH:9][C:8]([S:11][CH3:12])=[CH:7][CH:6]=1)=O.[Cl-].[OH:16][NH3+:17].C([O-])(=O)C.[Na+]>C(O)C.O>[F:1][C:2]([F:14])([F:13])[C:3]([C:5]1[CH:10]=[CH:9][C:8]([S:11][CH3:12])=[CH:7][CH:6]=1)=[N:17][OH:16]

Participants

6

Reactant 3

HCID 21645Hydroxylamine HClHCID 517045Sodium AcetateHCID 27606164'-thiomethyl-2,2,2-trifluoroacetophenone

Product 1

HCID 59115139HCID 59115139, compoundYield 54%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

49.3 g (224 mmol) of 2,2,2-trifluoro-1-(4-methylsulfanyl-phenyl)-ethanone are dissolved in 250 ml of hot ethanol. To this solution is added dropwise a solution of hydroxylammonium chloride (16.3 g, 235 mmol) and sodium acetate (31.2 g, 381 mmol) in 125 ml of water, and the reaction solution is stirred under reflux for 6.5 hr. The reaction mixture was concentrated by rotary evaporation and poured into ice/water. The resulting yellow solid is filterd and washed with water. After drying under reduced pressure, recrystallization from hexane-ethyl acetate affords 28.4 g of white solid (54%). The structure is confirmed by the 1H-NMR spectrum (CDCl3), δ[ppm]:: d 2.51 (s, 3H), 7.31 (d, 2H), 7.49 (d, 2H), 8.80 (broad s, 1H).

Workup

  1. temperatureunder reflux for 6.5 hr
  2. concentrationThe reaction mixture was concentrated by rotary evaporation
  3. additionpoured into ice/water
  4. washwashed with water
  5. dry with materialAfter drying under reduced pressure, recrystallization from hexane-ethyl acetate

Sources & evidence

ORD record
ord-a16d994533da42cbab56bba4b6f2f8d7
Source dataset
uspto-grants-2003_07
Patent number
US06596445B1

Reaction notes

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