Hydroxylamine HCl → HCID 73422950, compound

HRID 1358163Notes

Reaction equation

HRID 1358163 reaction equation
[Cl-].[OH:2][NH3+:3].C([O-])(=O)C.[Na+].[CH3:9][S:10][C:11]1[CH:16]=[CH:15][C:14]([C:17](=O)[CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[CH:13][CH:12]=1>O.C(O)C>[CH3:9][S:10][C:11]1[CH:16]=[CH:15][C:14]([C:17](=[N:3][OH:2])[CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[CH:13][CH:12]=1

Participants

6

Reactant 3

HCID 21645Hydroxylamine HClHCID 517045Sodium AcetateHCID 27600881-(4-(methylthio)phenyl)-2-phenylethanone

Product 1

HCID 73422950HCID 73422950, compoundYield 71%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

Hydroxylammonium chloride (4.19 g, 60.2 mmol) and sodium acetate (7.42 g, 90.4 mmol) are dissolved in 20 ml of water. To this solution 9.72 g (40.1 mmol) of 1-(4-methylsulfanyl-phenyl)-2-phenyl-ethanone in 60 ml of ethanol are added. The reaction mixture is heated to reflux for 18.5 hr. The reaction mixture was concentrated by rotary evaporation and poured into water. The resulting white solid is filterd and washed with water. After drying under reduced pressure, recrystallization from hexane-CH2Cl2 affords 7.32 g of a white solid (71%). 1H NMR (CDCl3), δ[ppm]: d 2.45 (s, 3H), 4.20 (s, 2H), 7.16-7.20 (m, 3H), 7.24-7.27 (m, 4H), 7.54 (d, 2H), 9.03 (s, 1H).

Workup

  1. temperatureThe reaction mixture is heated
  2. temperatureto reflux for 18.5 hr
  3. concentrationThe reaction mixture was concentrated by rotary evaporation
  4. additionpoured into water
  5. washwashed with water
  6. dry with materialAfter drying under reduced pressure, recrystallization from hexane-CH2Cl2

Sources & evidence

ORD record
ord-c1377ab7fd3a4742b4df2404215eb65a
Source dataset
uspto-grants-2003_07
Patent number
US06596445B1

Reaction notes

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