Hydroxyamine hydrochloride → HCID 131715509, compound

HRID 1905027Notes

Reaction equation

HRID 1905027 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-4e027a9cc11d436382b59784ec02358d
Source dataset
uspto-grants-1989_06
Patent number
US04841056

Reaction notes

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