Hydrochloric Acid → 1-(2-Thioxo-2,3-dihydrobenzo[d]thiazol-5-yl)ethanone

HRID 1595167

Reaktionsgleichung

Reaktionsgleichung von HRID 1595167
[C:1]([C:4]1[CH:5]=[CH:6][C:7]2[S:11][C:10](Cl)=[N:9][C:8]=2[CH:13]=1)(=[O:3])[CH3:2].[SH2:14].[K].Cl>C(O)C>[C:1]([C:4]1[CH:5]=[CH:6][C:7]2[S:11][C:10](=[S:14])[NH:9][C:8]=2[CH:13]=1)(=[O:3])[CH3:2]

Komponenten

5

Edukt 3

HCID 313Hydrochloric AcidHCID 217036431-(2-Chlorobenzo[d]thiazol-5-yl)ethanoneHCID 86743134Potassium hydrogensulfide

Produkt 1

HCID 217036441-(2-Thioxo-2,3-dihydrobenzo[d]thiazol-5-yl)ethanoneAusbeute 80,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

A mixture of 5-acetyl-2-chlorobenzothiazole (137 mg, 0.65 mmol), potassium hydrogen sulfide (94 mg, 1.30 mmol) and ethanol (3.3 mL) in a capped flask was stirred in an oil bath at 80° C. for two hours. The mixture was cooled in ice, acidified with 1N hydrochloric acid (1.35 mL) and evaporated in vacuo. The residue was partitioned between water (25 mL) and ethyl acetate (50, 25 mL). The organic extracts were washed with brine, dried over magnesium sulfate, filtered and evaporated in vacuo to a solid (133 mg). This material was triturated with ether and dried to provide 5-acetyl-2-thioxo-2,3-dihydrobenzothiazole (110 mg) as a pale yellow solid.

Aufarbeitung

  1. temperatureThe mixture was cooled in ice
  2. customevaporated in vacuo
  3. customThe residue was partitioned between water (25 mL) and ethyl acetate (50, 25 mL)
  4. washThe organic extracts were washed with brine
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. customevaporated in vacuo to a solid (133 mg)
  8. customThis material was triturated with ether
  9. customdried

Quellen und Nachweise

ORD-Eintrag
ord-9b36e4436751483e9091064a182868fc
Quelldatensatz
uspto-grants-2001_09
Patentnummer
US06288054B1

Verknüpfte Notizen

Wird geladen…