Reaktion #1859544

Reaktionsgleichung

hydrazine

(1S,2R)-5′-(4-chlorophenyl)-2,6′,7′-trimethylspiro[cyclopropane-1,3′-thieno[2,3-e][1,4]diazepin]-2′(1′H)-one

Toluene

Lawesson's Reagent

→

(1S,2R)-5′-(4-chlorophenyl)-2′-hydrazono-2,6′,7′-trimethyl-1′,2′-dihydrospiro[cyclopropane-1,3′-thieno[2,3-e][1,4]diazepine]

Ausbeute 82.8%

Lösungsmittel

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturthe reaction was cooled
2. 2
   workup.STIRRINGThe reaction was stirred at room temperature
3. 3
   Einengenbefore being concentrated
4. 4
   Sonstigepurified by column chromatography

Vorschrift

A round bottomed flask was charged with (1S,2R)-5′-(4-chlorophenyl)-2,6′,7′-trimethylspiro[cyclopropane-1,3′-thieno[2,3-e][1,4]diazepin]-2′(1′H)-one (289 mg, 0.838 mmol) and a stir bar. Toluene (8.5 mL, 0.1 M) added, followed by Lawesson's Reagent (186 mg, 0.461 mmol), and the reaction was stirred at 110° C. After conversion to the thioamide intermediate, as determined by LC/MS, the reaction was cooled and diluted with THF (20 mL) for the addition of hydrazine (263 μl, 8.38 mmol). The reaction was stirred at room temperature before being concentrated and purified by column chromatography to give (1S,2R)-5′-(4-chlorophenyl)-2′-hydrazono-2,6′,7′-trimethyl-1′,2′-dihydrospiro[cyclopropane-1,3′-thieno[2,3-e][1,4]diazepine] (249 mg). LRMS (M+H)+: 359 m/z

Quelle