Hydrochloric Acid → 2-(1-Hydroxaminoethyl)phenoxathiin

HRID 1087380

Reaktionsgleichung

Reaktionsgleichung von HRID 1087380
[N:1](=[C:3]([C:5]1[CH:18]=[CH:17][C:16]2[O:15][C:14]3[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=3)[S:8][C:7]=2[CH:6]=1)[CH3:4])[OH:2].B.N1C=CC=CC=1.Cl>C(O)C>[NH:1]([CH:3]([C:5]1[CH:18]=[CH:17][C:16]2[O:15][C:14]3[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=3)[S:8][C:7]=2[CH:6]=1)[CH3:4])[OH:2]

Komponenten

5

Edukt 3

HCID 313Hydrochloric AcidHCID 5151822-(1-Hydroximinoethyl)phenoxathiinHCID 2723995Borane;pyridine

Produkt 1

HCID 156610132-(1-Hydroxaminoethyl)phenoxathiinAusbeute 89,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

The oxime from Step 1 (450 mg, 1.75 mmol) was suspended in ethanol (9 mL) and, at 0° C., there was added pyridine-borane (325 mg, 3.5 mmol) and 4M ethanolic hydrogen chloride (HCl) (1.33 mL, 5.32 mmol). The mixture was stirred at 0° C. for 20 minutes, then at room temperature for 1 hour. The ethanol was evaporated and the residue partitioned between water and ether. The aqueous portion was basified with 1N aqueous sodium hydroxide and extracted twice with ether. Drying of the ether and evaporation afforded the title product (408 mg) as an oil which slowly became a white solid, m.p.: 64°-67° C.

Aufarbeitung

  1. waitat room temperature for 1 hour
  2. customThe ethanol was evaporated
  3. customthe residue partitioned between water and ether
  4. extractionextracted twice with ether
  5. dry with materialDrying of the ether and evaporation

Quellen und Nachweise

ORD-Eintrag
ord-e653b95f47a446148c1ae41f2403e257
Quelldatensatz
uspto-grants-1991_07
Patentnummer
US05036067

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