Hydroxyamine hydrochloride → HCID 58044204, compound

HRID 1919129Notes

Reaction equation

HRID 1919129 reaction equation
[NH2:1][OH:2].Cl.CC(O[Na])=O.[C:9]12[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[S:15][C:14]1[C:13](=O)[CH2:12][CH2:11][C:10]2=1>CO>[C:9]12[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[S:15][C:14]1/[C:13](=[N:1]\[OH:2])/[CH2:12][CH2:11][C:10]2=1

Participants

5

Reactant 3

HCID 443297Hydroxyamine hydrochlorideHCID 58044291HCID 58044291, compoundHCID 178418247HCID 178418247, compound

Product 1

HCID 58044204HCID 58044204, compoundYield 92.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of NH2OH.HCl (18.4 g, 266 mmol) in MeOH (600 mL) at 0° C. was slowly added CH3COONa (21.8 g, 266 mmol). After stirring at 0° C. for 30 min, 329d (10 g, 53 mmol) was added. The reaction solution was allowed to warm to room temperature and stirred for overnight. It was then evaporated in vacuo. 100 mL of water was added to the residue and the resulting mixture was extracted with ethyl acetate (500 mL×3). The organic layers were combined, washed with brine (50 mL), and dried over sodium sulfate. The drying agent was removed by filtration and the filtrate was concentrated under reduced pressure to give 329e as a yellow solid (10 g, 92%). MS: [M+H]+ 203.

Workup

  1. customat 0° C.
  2. temperatureto warm to room temperature
  3. stirringstirred for overnight
  4. customIt was then evaporated in vacuo
  5. addition100 mL of water was added to the residue
  6. extractionthe resulting mixture was extracted with ethyl acetate (500 mL×3)
  7. washwashed with brine (50 mL)
  8. dry with materialdried over sodium sulfate
  9. customThe drying agent was removed by filtration
  10. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-a61889a0d3e04bc18bdb51e46d783d8f
Source dataset
uspto-grants-2013_12
Patent number
US08618107B2

Reaction notes

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