Reaktion #78294

Reaktionsgleichung

Water

4-chloro-3-(3-methyl-2-butenyloxy)benzenamine

triethylamine

2-methyl-3-furancarboxylic chloride

→

4-chloro-3-(3-methyl-2-butenyloxy)phenyl-2-methyl-3-furancarboxamide

Lösungsmittel

methylene chloride

methylene chloride

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturwas maintained at −5° C. to 0° C
2. 2
   workup.ADDITIONWhen the addition
3. 3
   Sonstigethe resultant reaction mixture
4. 4
   workup.WAITleft
5. 5
   workup.STIRRINGstirring for 15 hours
6. 6
   Sonstigethe organic layer separated
7. 7
   Waschenwashed successively with water, dilute hydrochloric acid, water, aqueous sodium bicarbonate, and water
8. 8
   TrocknenAfter drying (MgSO4)
9. 9
   Sonstigethe solvent was removed from the washed organic layer
10. 10
    Sonstigethe residue was recrystallised from isopropyl alcohol

Vorschrift

A first solution of 2-methyl-3-furancarboxylic chloride (13.57 g) in methylene chloride (94 mL) was stirred in an ice/salt bath. A second solution of 4-chloro-3-(3-methyl-2-butenyloxy)benzenamine (19.8 g), triethylamine (14 mL) in methylene chloride (94 mL) was added to the first solution at such a rate that the temperature was maintained at −5° C. to 0° C. When the addition was complete, the resultant reaction mixture was stirred to ambient temperature and left stirring for 15 hours. Water was added to the reaction mixture and then the organic layer separated and washed successively with water, dilute hydrochloric acid, water, aqueous sodium bicarbonate, and water. After drying (MgSO4), the solvent was removed from the washed organic layer and the residue was recrystallised from isopropyl alcohol to give N-[4-chloro-3-(3-methyl-2-butenyloxy)phenyl-2-methyl-3-furancarboxamide, a white solid, 17 g. A second crop of beige crystals, 7.6 g, was also obtained.

Quelle