반응 #1743197

반응 방정식

triethylamine

2-(4-chlorophenyl)-2-[(1,2,4-triazol-1-yl)methyl]hexanoic acid

tert-butanol

diphenylphosphorylazide

→

azide

수율 47.0%

2-(4-Chlorophenyl)-2-[(1,2,4-triazol-1-yl)methyl]hexanoylazide

수율 47.0%

용매

dimethylformamide

dimethylformamide

반응 조건

후처리

1. 1
   온도to warm to room temperature
2. 2
   workup.ADDITIONAddition of ice
3. 3
   기타the precipitation of the product
4. 4
   여과Filtration
5. 5
   기타gave 1.10 g of a crude product which
6. 6
   기타was carefully recrystallized from a 1 to 3 mixture of ethyl acetate and hexane

실험 절차

To a stirred solution of 1.0 g (3.25 mmols) of 2-(4-chlorophenyl)-2-[(1,2,4-triazol-1-yl)methyl]hexanoic acid in 3 mL of dimethylformamide was added 0.30 mL of tert-butanol. This solution was cooled to 0° C. and a solution of 1.07 g (3.90 mmols) of diphenylphosphorylazide in 1 mL of dimethylformamide was added followed by 0.72 mL (7.15 mmols) of triethylamine. The resultant mixture was stirred for 2 hours and then allowed to warm to room temperature and stirred for an additional 15 hours. Addition of ice caused the precipitation of the product. Filtration gave 1.10 g of a crude product which was carefully recrystallized from a 1 to 3 mixture of ethyl acetate and hexane to afford 0.46 g (47%) of azide as a white crystalline solid, melting point 100°-101° C.: 1H-NMR (CDCl3, Me4Si) 0.7-1.1 (t, J=6 Hz, CH2 --CH3), 1.1-1.7 (m), 1.75-2.1 (m), 4.6 (d, CH2 --N), 6.8-7.2(m,phenyl H), 7.3 (s,CH=N), 7.7 ppm (s,CH=N):

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