Hydrochloric Acid → 4-hydroxy-N-[4-(methylsulfinyl)-1,3-thiazol-2-yl]benzamide

HRID 1620883Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1620883
Cl.C([O:5][C:6]1[CH:11]=[CH:10][C:9]([C:12](=[O:22])[NH:13][C:14]2[S:15][CH:16]=[C:17]([S:19]([CH3:21])=[O:20])[N:18]=2)=[CH:8][CH:7]=1)(=O)C>O1CCCC1>[OH:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]([NH:13][C:14]2[S:15][CH:16]=[C:17]([S:19]([CH3:21])=[O:20])[N:18]=2)=[O:22])=[CH:8][CH:7]=1

Komponenten

4

Edukt 2

HCID 313Hydrochloric AcidHCID 569693894-{[4-(Methylsulfinyl)-1,3-thiazol-2-yl]carbamoyl}phenyl acetate

Produkt 1

HCID 569693904-hydroxy-N-[4-(methylsulfinyl)-1,3-thiazol-2-yl]benzamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

2 M hydrochloric acid (3.0 mL) is added to a suspension of 3 (0.12 g, 0.33 mmol) in tetrahydrofuran (3.0 mL), and the resulting suspension is warmed to reflux. The reaction becomes homogeneous upon heating. After refluxing for 1.5 h, the reaction is allowed to cool to room temperature, and is then partitioned between diethyl ether and water. The ether layer is washed with water, saturated aqueous sodium bicarbonate, and brine. The ether layer is dried with anhydrous sodium sulfate and concentrated in vacuo. The residue is triturated with ethyl acetate, the solvent is removed under a stream of nitrogen, and the resulting solid is dried in vacuo at 55° C. to give 4 as a light yellow solid.

Aufarbeitung

  1. temperaturethe resulting suspension is warmed to reflux
  2. temperatureupon heating
  3. temperatureAfter refluxing for 1.5 h
  4. customis then partitioned between diethyl ether and water
  5. washThe ether layer is washed with water, saturated aqueous sodium bicarbonate, and brine
  6. dry with materialThe ether layer is dried with anhydrous sodium sulfate
  7. concentrationconcentrated in vacuo
  8. customThe residue is triturated with ethyl acetate
  9. customthe solvent is removed under a stream of nitrogen
  10. customthe resulting solid is dried in vacuo at 55° C.

Quellen und Nachweise

ORD-Eintrag
ord-fc19431417ff415fac5580dbeab6cd1f
Quelldatensatz
uspto-grants-2014_07
Patentnummer
US08772502B2

Notizen zur Reaktion

Wird geladen…