Reaktion #1859511

Reaktionsgleichung

acetic acid chloride

5-(4-chlorophenyl)-3,3,6,7-tetramethyl-1H-thieno[2,3-e][1,4]diazepine-2(3H)-thione

hydrazine hydrate

Triethylamine

→

(Z)—N′-(5-(4-chlorophenyl)-3,3,6,7-tetramethyl-1H-thieno[2,3-e][1,4]diazepin-2(3H)-ylidene)acetohydrazide

Lösungsmittel

Tetrahydrofuran

dichloromethane

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigeconsumption of the starting material
2. 2
   workup.STIRRINGthe solution stirred at rt 1 h
3. 3
   Einengenconcentrated for purification by column chromatography (eluting with dichloromethane/methanol/ammonium hydroxide), which

Vorschrift

A round bottomed flask was charged with 5-(4-chlorophenyl)-3,3,6,7-tetramethyl-1H-thieno[2,3-e][1,4]diazepine-2(3H)-thione (123 mg, 0.353 mmol) and a stir bar. Tetrahydrofuran (10 mL, 0.05 M) was added, and the solution was cooled to 0° C. for the addition of hydrazine hydrate (132 μl, 1.763 mmol). Stirred at room temperature 30 min, at which point both TLC and LC/MS analysis indicated essentially complete consumption of the starting material. Triethylamine (295 μl, 2.115 mmol, 6 equiv) was added, followed by acetic acid chloride (150 μl, 2.115 mmol, 6 equiv) (careful! exothermic!), and the solution stirred at rt 1 h. The solution was diluted with dichloromethane and concentrated for purification by column chromatography (eluting with dichloromethane/methanol/ammonium hydroxide), which yielded (Z)—N′-(5-(4-chlorophenyl)-3,3,6,7-tetramethyl-1H-thieno[2,3-e][1,4]diazepin-2(3H)-ylidene)acetohydrazide as a dark red oil (m/z=389) that was used in the subsequent reaction.

Quelle