Potassium Hydroxide → 1-Benzhydryl-3-(thiophen-2-ylthio)-azetidine

HRID 83073

Reaktionsgleichung

Reaktionsgleichung von HRID 83073
[OH-].[K+].[S:3]1[CH:7]=[CH:6][CH:5]=[C:4]1[SH:8].CS(O[CH:14]1[CH2:17][N:16]([CH:18]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH2:15]1)(=O)=O>C1COCC1>[CH:18]([N:16]1[CH2:17][CH:14]([S:8][C:4]2[S:3][CH:7]=[CH:6][CH:5]=2)[CH2:15]1)([C:25]1[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=1)[C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1

Komponenten

5

Edukt 3

HCID 14797Potassium Hydroxide2×HCID 5226742-Thiophenethiol2×HCID 27587161-(Diphenylmethyl)azetidin-3-yl methanesulfonate

Produkt 1

HCID 671546111-Benzhydryl-3-(thiophen-2-ylthio)-azetidine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

Potassium hydroxide (141 mg, 2.52 mmol) and thiophene-2-thiol (292 mg, 238 μL) were added to a solution of 1-benzhydrylazetidin-3-yl methanesulfonate (400 mg, 1.26 mmol) solubilized in THF (7 mL). The reaction mixture was stirred a first time under microwave irradiations (100 W) at 80° C. for 30 minutes. Potassium hydroxide (141 mg, 2.52 mmol) and thiophene-2-thiol (292 mg, 238 μL) were added and the reaction mixture was stirred for a second time under microwave irradiations (100 W) at 80° C. for 30 minutes. After concentration to dryness, the residue was purified by chromatography on silica gel using petroleum ether/ethyl acetate (1:0 to 9:1) as eluent. The title product was obtained as a yellow solid (160 mg, 37%).

Aufarbeitung

  1. stirringthe reaction mixture was stirred for a second time under microwave irradiations (100 W) at 80° C. for 30 minutes
  2. concentrationAfter concentration to dryness
  3. customthe residue was purified by chromatography on silica gel

Quellen und Nachweise

ORD-Eintrag
ord-ad9462dac0964153bcf443371ef3345c
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08846711B2

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