Reaktion #704361

Reaktionsgleichung

3,4-methylenedioxyphenylacetic acid

thionyl chloride

→

3,4-methylenedioxyphenylacetyl chloride

Lösungsmittel

chloroform

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturThe mixture was refluxed for about 3 hours
2. 2
   Sonstigewas evaporated
3. 3
   workup.ADDITIONToluene was added to the residue
4. 4
   Sonstigethe mixture was evaporated
5. 5
   Sonstigeto remove the excess of thionyl chloride
6. 6
   workup.ADDITIONTo the residue was added dichloromethane (3 ml)

Vorschrift

To a suspension of 3,4-methylenedioxyphenylacetic acid (569 mg, 3.16 mmol) in chloroform (6 ml) was added thionyl chloride (1.2 ml). The mixture was refluxed for about 3 hours, and was evaporated. Toluene was added to the residue and the mixture was evaporated to remove the excess of thionyl chloride. To the residue was added dichloromethane (3 ml) to give a dichloromethane solution of 3,4-methylenedioxyphenylacetyl chloride. To an ice-cold mixture of 2-amino-4-(4-piperidinyl)quinazoline (600 mg, 2.63 mmol) and triethylamine (319 mg, 3.16 mmol) in dichloromethane (16 ml) was added dropwise the solution of 3,4-methylenedioxyphenylacetyl chloride prepared above under a nitrogen atmosphere. The mixture was stirred for about two hours and to the reaction mixture was added dichloromethane and saturated sodium hydrogencarbonate aqueous solution followed by extraction. The organic layer was washed with water, and then dried over sodium sulfate and evaporated in vacuo. The residue was purified by silica gel column chromatography (dichloromethane:methanol=30:1). Crystallization from methanol gave the titled compound (617 mg).

Quelle