반응 #409571

반응 방정식

hydrochloric acid

2-(4-cyanophenyl)-4-[4-[3-(1-imidazolyl)propyl]phenoxymethyl]oxazole

sodium azide

ammonium chloride

→

5-[4-[4-[4-[3-(1-imidazolyl)propyl]phenoxymethyl]-2-oxazolyl]phenyl]-1H-tetrazole

수율 33.0%

용매

N,N-dimethylformamide

water

반응 조건

후처리

1. 1
   기타ranging from 130 to 135° C
2. 2
   여과The resulting crystalline precipitate was collected by filtration
3. 3
   추출The filtrate was subjected to extraction with ethyl acetate-tetrahydrofuran
4. 4
   세척The organic layer was washed with water
5. 5
   건조dried (MgSO4)
6. 6
   농축concentrated
7. 7
   기타to leave a crystalline product
8. 8
   기타recrystallized from methanol

실험 절차

A mixture of 2-(4-cyanophenyl)-4-[4-[3-(1-imidazolyl)propyl]phenoxymethyl]oxazole (700 mg), sodium azide (585 mg), ammonium chloride (480 mg) and N,N-dimethylformamide (20 ml) was stirred for 24 hours at temperatures ranging from 130 to 135° C. The reaction mixture was poured into water, which was neutralized with 1N hydrochloric acid. The resulting crystalline precipitate was collected by filtration. The filtrate was subjected to extraction with ethyl acetate-tetrahydrofuran. The organic layer was washed with water, dried (MgSO4), and concentrated to leave a crystalline product. Both crystalline products were combined and recrystallized from methanol to give 5-[4-[4-[4-[3-(1-imidazolyl)propyl]phenoxymethyl]-2-oxazolyl]phenyl]-1H-tetrazole (250 mg, 33%) as colorless prisms, mp 273-275° C. (decomp.).

출처