Hydroxyamine hydrochloride → HCID 131715509, compound

HRID 1252172Notes

Reaction equation

HRID 1252172 reaction equation
[C:1]([CH:4]1[CH:18]2[CH:7]([CH2:8][C:9]3[C:17]4[C:16]2=[CH:15][CH:14]=[CH:13][C:12]=4[N:11]([S:19]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)(=[O:21])=[O:20])[CH:10]=3)[N:6]([CH3:28])[CH2:5]1)(=O)C.C([O-])(=O)C.[Na+].Cl.[NH2:35][OH:36]>CO>[C:22]1([S:19]([N:11]2[C:12]3[CH:13]=[CH:14][CH:15]=[C:16]4[CH:18]5[CH:7]([C:8](=[N:35][OH:36])[C:9]([C:17]=34)=[CH:10]2)[N:6]([CH3:28])[CH2:5][CH:4]5[CH3:1])(=[O:20])=[O:21])[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

5

Reactant 3

HCID 443297Hydroxyamine hydrochlorideHCID 517045Sodium AcetateHCID 13576795HCID 13576795, compound

Product 1

HCID 131715509HCID 131715509, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirred solution of the 9-acetyl compound of Example 4 (0.25 g) in methanol (12 cm3) was added anhydrous sodium acetate (0.078 g) and hydroxylamine hydrochloride (0.0615 g) and the orange solution heated to reflux. After 5 hours reaction was indicated to be complete, all solvents were removed under vacuum. Chloroform (40 cm3) and water (40 cm3) was added and the residue partitioned. The organic layer was re-washed with water (25 cm3), dried and evaporated under vacuum to give a yellow-white solid.

Workup

  1. temperaturethe orange solution heated to reflux
  2. customAfter 5 hours reaction
  3. customall solvents were removed under vacuum
  4. additionChloroform (40 cm3) and water (40 cm3) was added
  5. customthe residue partitioned
  6. washThe organic layer was re-washed with water (25 cm3)
  7. customdried
  8. customevaporated under vacuum
  9. customto give a yellow-white solid

Sources & evidence

ORD record
ord-5e6cf7efa8824d71b8a0a640addefd5e
Source dataset
uspto-grants-1988_05
Patent number
US04742075

Reaction notes

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