Hydroxyamine hydrochloride → HCID 72612001, compound

HRID 351974Notes

Reaction equation

HRID 351974 reaction equation
[Cl:1][CH2:2][CH2:3][CH2:4][CH2:5][N:6]1[C:10]2[C:11](=O)[CH2:12][CH2:13][N:14]([CH3:18])[S:15](=[O:17])(=[O:16])[C:9]=2[CH:8]=[CH:7]1.Cl.[NH2:21][OH:22].C([O-])(=O)C.[Na+]>C(O)C>[Cl:1][CH2:2][CH2:3][CH2:4][CH2:5][N:6]1[C:10]2[C:11](=[N:21][OH:22])[CH2:12][CH2:13][N:14]([CH3:18])[S:15](=[O:17])(=[O:16])[C:9]=2[CH:8]=[CH:7]1

Participants

5

Reactant 3

HCID 443297Hydroxyamine hydrochlorideHCID 517045Sodium AcetateHCID 22714959HCID 22714959, compound

Product 1

HCID 72612001HCID 72612001, compoundYield 73%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A suspension of 152 mg (0.5 mmol) of Compound 18, 174 mg (2.5 mmol) of hydroxylamine hydrochloride and 205 mg (2.5 mmol) of sodium acetate in 20 ml of ethanol was refluxed for 20 hours. The reaction mixture was concentrated under reduced pressure, followed by the addition of water to the residue. The resulting mixture was extracted with chloroform (3 times). The organic layer was washed with a saturated aqueous solution of sodium chloride, dried over anhydrous sodium sulfate, and then concentrated under reduced pressure. The residue was purified by chromatography on a silica gel column (eluent: methanol/chloroform=3/97), whereby 116 mg of the title compound were obtained (yield: 73%).

Workup

  1. temperaturewas refluxed for 20 hours
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. additionfollowed by the addition of water to the residue
  4. extractionThe resulting mixture was extracted with chloroform (3 times)
  5. washThe organic layer was washed with a saturated aqueous solution of sodium chloride
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified by chromatography on a silica gel column (eluent: methanol/chloroform=3/97)

Sources & evidence

ORD record
ord-2f36da7f6c8c47ef90aba16d8f94d510
Source dataset
uspto-grants-2004_06
Patent number
US06743913B2

Reaction notes

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