반응 #78294

반응 방정식

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

용매

methylene chloride

methylene chloride

반응 조건

후처리

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

실험 절차

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.

출처