Hydroxyamine hydrochloride → HCID 88259102, compound

HRID 1003970Notes

Reaction equation

HRID 1003970 reaction equation
Cl.[NH2:2][OH:3].O=[C:5]([C:10]1[C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=2[S:12][CH:11]=1)[C:6]([O:8][CH3:9])=[O:7]>CO>[OH:3][N:2]=[C:5]([C:10]1[C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=2[S:12][CH:11]=1)[C:6]([O:8][CH3:9])=[O:7]

Participants

4

Reactant 2

HCID 443297Hydroxyamine hydrochlorideHCID 54398307HCID 54398307, compound

Product 1

HCID 88259102HCID 88259102, compoundYield 73.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Hydroxylarnine hydrochloride (503 mg) was added to a stirred solution of methyl 2-oxo-2-(3-benzothienyl)acetate (790 mg) in methanol (30 ml). When all the solid had dissolved the mixture was allowed to stand overnight. The solvent was evaporated and the residue partitioned between ethyl acetace and water. The organic phase was washed with water and brine, dried over magnesium sulphate and evaporated. The title oxime (622 mg) was isolated as a mixture of isomers by column chromatography of the residue (Kieselgel: 3:1 going to 1:1 hexane:ethyl acetate. νmax (CHCl3)/cm-1 3568, 3296, 1737. δH (250 MHz, CDCl3), 3.90 and 4.00 (3H, two s's), 7.37-7.59 (2H, m), 7.61 and 7.77 (1H, two s's), 8.30 and 9.15 (1H, two broad s's), 8.43-8.47 (1H, m); m/z (EI) 235 (M+).

Workup

  1. dissolutionWhen all the solid had dissolved the mixture
  2. customThe solvent was evaporated
  3. customthe residue partitioned between ethyl acetace and water
  4. washThe organic phase was washed with water and brine
  5. dry with materialdried over magnesium sulphate
  6. customevaporated

Sources & evidence

ORD record
ord-2e6f6617547c478e978845ff2c126630
Source dataset
uspto-grants-2000_04
Patent number
US06048852

Reaction notes

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