Ethanol → 2-(1-Hydroximinoethyl)phenoxathiin

HRID 1087379

Reaction equation

HRID 1087379 reaction equation
[C:1]([C:4]1[CH:17]=[CH:16][C:15]2[O:14][C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[S:7][C:6]=2[CH:5]=1)(=O)[CH3:2].Cl.[NH2:19][OH:20].C(O)C>N1C=CC=CC=1>[N:19](=[C:1]([C:4]1[CH:17]=[CH:16][C:15]2[O:14][C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[S:7][C:6]=2[CH:5]=1)[CH3:2])[OH:20]

Participants

5

Reactant 3

HCID 702EthanolHCID 443297Hydroxyamine hydrochlorideHCID 5151742-Acetylphenoxathiin

Product 1

HCID 5151822-(1-Hydroximinoethyl)phenoxathiinYield 90.4%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A mixture of 2-acetylphenoxathiin (J.A.C.S. 1936, 58, 717) (484 mg, 2 mmol), hydroxylamine hydrochloride (556 mg, 8 mmol), ethanol (8 mL) and pyridine (4 mL) was stirred at room temperature for 45 minutes. The ethanol was evaporated and the residue triturated with water until a solid was obtained. Filtration afforded the title oxime (465 mg) as a cream-colored solid, m.p.: 143°-148° C.

Workup

  1. customThe ethanol was evaporated
  2. customthe residue triturated with water until a solid
  3. customwas obtained
  4. filtrationFiltration

Sources & evidence

ORD record
ord-5c2ab80badb14bad881eb7da742595e0
Source dataset
uspto-grants-1991_07
Patent number
US05036067

Linked notes

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