Ethanol → 2-(Ethylthio)benzothiazole

HRID 2261900

Reaktionsgleichung

Reaktionsgleichung von HRID 2261900
[CH2:1](O)[CH3:2].[S:4]1[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[N:6]=[C:5]1[SH:13].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>O1CCCC1>[CH2:8]([S:4][C:5]1[S:13][C:2]2[CH:1]=[CH:10][CH:11]=[CH:12][C:7]=2[N:6]=1)[CH3:9]

Komponenten

5

Edukt 3

HCID 702EthanolHCID 11776TriphenylphosphineHCID 178418395HCID 178418395, Verbindung

Produkt 1

HCID 759932-(Ethylthio)benzothiazoleAusbeute 104,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

Ethyl alcohol (0.63 mL, 10.8 mmol), 2-benzothiazolethiol (2.0 g, 11.9 mmol) and triphenylphosphine (3.1 g, 11.9 mmol) were dissolved in tetrahydrofuran (50 mL) and cooled to 0° C. Then added diisopropylazadicarboxylate (2.3 mL, 11.9 mmol) and continued stirring for 1 hr. Upon completion, the reaction mixture was dried in vacuo, filtered through a plug of silica with 5% ethyl acetate in hexane and dried in vacuo again to yield 2-(ethylthio)-1,3-benzothiazole (2.2 g, HPLC RT=3.05 min.). LC-MS m/z=196.

Aufarbeitung

  1. additionThen added diisopropylazadicarboxylate (2.3 mL, 11.9 mmol)
  2. customUpon completion, the reaction mixture was dried in vacuo
  3. filtrationfiltered through a plug of silica with 5% ethyl acetate in hexane
  4. customdried in vacuo again

Quellen und Nachweise

ORD-Eintrag
ord-859ea284631c4e34b55afa16fcf3b1c8
Quelldatensatz
uspto-grants-2010_12
Patentnummer
US07847100B2

Verknüpfte Notizen

Wird geladen…