반응 #4878

반응 방정식

methanesulfonylchloride

1-methyl-3-pyrrolidinol

triethylamine

sodium

1-hydroxy-2-naphthalenecarboxamide

→

1-[(1-Methyl-3-pyrrolidinyl)oxy]-2-naphthalene carboxamide

용매

water

benzene

반응 조건

후처리

1. 1
   온도while cooling with an ice bath
2. 2
   여과filtered
3. 3
   세척The filter cake was washed with 500 ml of benzene
4. 4
   농축concentrated on the rotary evaporator to about 200 ml
5. 5
   workup.ADDITIONThe residue was added dropwise to the
6. 6
   기타above prepared dimethylsulfoxide solution
7. 7
   workup.STIRRINGwhile stirring at 75° C
8. 8
   온도The resulting solution was cooled
9. 9
   추출The mixture was extracted with three portions of chloroform
10. 10
    농축concentrated
11. 11
    기타The residue was partitioned between ethyl acetate and dilute hydrochloric acid
12. 12
    추출extracted twice with ethyl acetate
13. 13
    건조dried over sodium sulfate
14. 14
    농축concentrated
15. 15
    기타The residue was crystallized from ethyl acetate-isooctane
16. 16
    기타A portion was recrystallized twice from ethyl acetate-isooctane, m.p. 122°-129° C.

실험 절차

In another vessel, 79 g (0.69 mole) of methanesulfonylchloride was added dropwise to a solution of 69.7 g (0.69 mole) of 1-methyl-3-pyrrolidinol and 77 g (0.76 mole) of triethylamine in 500 ml of dry benzene while cooling with an ice bath. The mixture was stirred 15 minutes and filtered. The filter cake was washed with 500 ml of benzene and the benzene filtrates were combined and concentrated on the rotary evaporator to about 200 ml. The residue was added dropwise to the above prepared dimethylsulfoxide solution containing the sodium salt of 1-hydroxy-2-naphthalenecarboxamide while stirring at 75° C. The temperature was maintained at 75° C. for 18 hr with external heat. The resulting solution was cooled and an equal volume of water was added. The mixture was extracted with three portions of chloroform. The washes were combined and concentrated. The residue was partitioned between ethyl acetate and dilute hydrochloric acid. The acid layer was made basic with sodium hydroxide and extracted twice with ethyl acetate. The ethyl acetate washes were combined, dried over sodium sulfate and concentrated. The residue was crystallized from ethyl acetate-isooctane. Yield of solid was 55 g (32%). A portion was recrystallized twice from ethyl acetate-isooctane, m.p. 122°-129° C.

출처