Hydroxylamine HCl → HCID 73422951, compound

HRID 1358161Notes

Reaction equation

HRID 1358161 reaction equation
[Cl-].[OH:2][NH3+:3].C([O-])(=O)C.[Na+].[F:9][C:10]([F:23])([F:22])[CH2:11][C:12]([C:14]1[CH:19]=[CH:18][C:17]([S:20][CH3:21])=[CH:16][CH:15]=1)=O>O.C(O)C>[F:9][C:10]([F:23])([F:22])[CH2:11][C:12]([C:14]1[CH:19]=[CH:18][C:17]([S:20][CH3:21])=[CH:16][CH:15]=1)=[N:3][OH:2]

Participants

6

Reactant 3

HCID 21645Hydroxylamine HClHCID 517045Sodium AcetateHCID 18183658HCID 18183658, compound

Product 1

HCID 73422951HCID 73422951, compoundYield 59.4%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

Hydroxylammonium chloride (1.07 g, 15.4 mmol) and sodium acetate (1.85 g, 22.5 mmol) are dissolved in 10 ml of water. To this solution are added 2.35 g (10.0 mmol) of 3,3,3-trifluoro-1-(4-methylsulfanyl-phenyl)-propan-1-one in 30 ml of ethanol. The reaction mixture is heated to reflux for 6.5 hr. The reaction mixture was concentrated by rotary evaporation and poured into water. The product is extracted with CH2Cl2, and the organic layer is washed with water, followed by drying over anhydrous MgSO4. After evaporation of the solvent, the product is purified by column chromatography on silica gel with CH2Cl2-Hexane (2:1) as eluent. 1.48 g of white solid melting at 106-107° C. are obtained (59%). 1H NMR (CDCl3), δ[ppm]: d 2.51 (s, 3H), 3.73 (q, 2H), 7.26 (d, 2H), 7.57 (d, 2H), 8.23 (s, 1H).

Workup

  1. temperatureThe reaction mixture is heated
  2. temperatureto reflux for 6.5 hr
  3. concentrationThe reaction mixture was concentrated by rotary evaporation
  4. additionpoured into water
  5. extractionThe product is extracted with CH2Cl2
  6. washthe organic layer is washed with water
  7. dry with materialby drying over anhydrous MgSO4
  8. customAfter evaporation of the solvent
  9. customthe product is purified by column chromatography on silica gel with CH2Cl2-Hexane (2:1) as eluent

Sources & evidence

ORD record
ord-6031c9dd86ca4d629b224ddac63843ca
Source dataset
uspto-grants-2003_07
Patent number
US06596445B1

Reaction notes

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