(R)-(-)-N-(2,3-Epoxypropyl)phthalimide → N-[(2R)-3-(1,3-benzothiazol-2-ylthio)-2-hydroxypropyl]-phthalimide

HRID 896633Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 896633
[O:1]1[CH2:3][C@H:2]1[CH2:4][N:5]1[C:9](=[O:10])[C:8]2=[CH:11][CH:12]=[CH:13][CH:14]=[C:7]2[C:6]1=[O:15].[SH:16][C:17]1[S:18][C:19]2[CH:25]=[CH:24][CH:23]=[CH:22][C:20]=2[N:21]=1>CCO>[S:18]1[C:19]2[CH:25]=[CH:24][CH:23]=[CH:22][C:20]=2[N:21]=[C:17]1[S:16][CH2:3][C@H:2]([OH:1])[CH2:4][N:5]1[C:9](=[O:10])[C:8]2=[CH:11][CH:12]=[CH:13][CH:14]=[C:7]2[C:6]1=[O:15]

Komponenten

4

Edukt 2

HCID 719415(R)-(-)-N-(2,3-Epoxypropyl)phthalimideHCID 178418395HCID 178418395, Verbindung

Produkt 1

HCID 10109719N-[(2R)-3-(1,3-benzothiazol-2-ylthio)-2-hydroxypropyl]-phthalimideAusbeute 59 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

A suspension of compound N-[(2R)-oxiran-2-ylmethyl]-phthalimide (21.1 g, 104 mmol) and 2-mercaptobenzothiazole (17.4 g, 104 mmol) in EtOH (600 mL) was heated to reflux for 16.5 h. The reaction was then cooled and concentrated under reduced pressure. The crude mixture was crystallized from ethanol and filtered to provide N-[(2R)-3-(1,3-benzothiazol-2-ylthio)-2-hydroxypropyl]-phthalimide (22.5 g, 59%) as a yellow solid. Data for N-[(2R)-3-(1,3-benzothiazol-2-ylthio)-2-hydroxypropyl]-phthalimide: 1H NMR (300 MHz, CDCl3) δ 7.88 (m, 2H), 7.75 (m, 4H), 7.45-7.26 (m, 2H), 5.18 (m, 1H), 4.42 (m, 1H), 4.08-3.88 (m, 2H), 3.61 (m, 1H), 3.42 (m, 1H).

Aufarbeitung

  1. temperaturewas heated
  2. temperatureto reflux for 16.5 h
  3. temperatureThe reaction was then cooled
  4. concentrationconcentrated under reduced pressure
  5. customThe crude mixture was crystallized from ethanol
  6. filtrationfiltered

Quellen und Nachweise

ORD-Eintrag
ord-96dbfd0653a3425b944af13f4ba8c9ad
Quelldatensatz
uspto-grants-2005_07
Patentnummer
US06919379B2

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