m-Chloroperbenzoic acid → 3-{[5-(Methylsulfinyl)-1,3-thiazol-2-yl]carbamoyl}phenyl acetate

HRID 1620887

Reaktionsgleichung

Reaktionsgleichung von HRID 1620887
ClC1C=CC=C(C(OO)=[O:9])C=1.[C:12]([O:15][C:16]1[CH:21]=[CH:20][CH:19]=[C:18]([C:22](=[O:31])[NH:23][C:24]2[S:25][C:26]([S:29][CH3:30])=[CH:27][N:28]=2)[CH:17]=1)(=[O:14])[CH3:13]>ClCCl>[C:12]([O:15][C:16]1[CH:21]=[CH:20][CH:19]=[C:18]([C:22](=[O:31])[NH:23][C:24]2[S:25][C:26]([S:29]([CH3:30])=[O:9])=[CH:27][N:28]=2)[CH:17]=1)(=[O:14])[CH3:13]

Komponenten

4

Edukt 2

HCID 70297m-Chloroperbenzoic acidHCID 575718763-{[5-(Methylsulfanyl)-1,3-thiazol-2-yl]carbamoyl}phenyl acetate

Produkt 1

HCID 569693943-{[5-(Methylsulfinyl)-1,3-thiazol-2-yl]carbamoyl}phenyl acetateAusbeute 106,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

A solution of m-chloroperbenzoic acid (0.458 g, 2.04 mmol, maximum 77%) is dissolved in dichloromethane (8.0 mL) and added dropwise over 15 minutes to a solution of 516 (0.630 g, 2.04 mmol) dissolved in dichloromethane (25.0 mL). The reaction is stirred at room temperature for 6 hours. The reaction is then partitioned between dichloromethane and saturated aqueous sodium thiosulfate. The organic layer is washed again with a saturated aqueous sodium thiosulfate, twice with saturated aqueous sodium bicarbonate and once with brine. The dichloromethane layer is dried over magnesium sulfate and concentrated in vacuo to give crude 8 (0.704 g, >100%), which is contaminated with traces of residual 3-chlorobenzoic acid. The crude product is re-dissolved in ethyl acetate and washed three times with a saturated aq. sodium bicarbonate, dried using magnesium sulfate and concentrated in vacuo to give a tan solid. The residue is dissolved in THF, and the light brown solution was filtered through a plug of Magnesol. The filter pad is washed well with THF, and the colorless filtrate is concentrated in vacuo to give 8 as a white solid.

Aufarbeitung

  1. customThe reaction is then partitioned between dichloromethane and saturated aqueous sodium thiosulfate
  2. washThe organic layer is washed again with a saturated aqueous sodium thiosulfate, twice with saturated aqueous sodium bicarbonate and once with brine
  3. dry with materialThe dichloromethane layer is dried over magnesium sulfate
  4. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-9144d066b07b4c629f868cbaba1f3e71
Quelldatensatz
uspto-grants-2014_07
Patentnummer
US08772502B2

Verknüpfte Notizen

Wird geladen…