反応 #81407

反応方程式

azide

sodium azide

N-tert-butyl 2-(3-bromo-2-oxo-5-phenyl-2,3,4,5-tetrahydro-1H-(1)benzazepin-1-yl) ethanoic acid amide

dimethylformamide

→

foam

収率 80.1%

N-tert-butyl-2-(3-azido-2-oxo-5-phenyl-2,3,4,5-tetrahydro-1H-(1)benzazepin-1-yl)ethanoic acid amide

収率 80.1%

溶媒

water

water

反応条件

後処理

1. 1
   その他To a 125 ml round-bottomed flask equipped with a nitrogen inlet
2. 2
   workup.DISSOLUTIONAfter dissolution
3. 3
   温度the solution heated at 80°-85° C. for 4 hours 20 minutes (at this point, tlc and NMR of an aliquot
4. 4
   温度The reaction was cooled
5. 5
   抽出extracted twice into ethyl acetate
6. 6
   洗浄The organic layer was washed with water and brine
7. 7
   乾燥dried over sodium sulfate
8. 8
   その他evaporated
9. 9
   その他The residue was chromatographed on silica gel using 3:1 hexane/ethyl acetate

実験手順

To a 125 ml round-bottomed flask equipped with a nitrogen inlet were added 8.2 grams (18.5 mmol) N-tert-butyl 2-(3-bromo-2-oxo-5-phenyl-2,3,4,5-tetrahydro-1H-(1)benzazepin-1-yl) ethanoic acid amide and 40 ml dimethylformamide. After dissolution, a solution of 1.44 grams (22.2 mmol) sodium azide in 2 mL water (with two additional 0.75 ml portions of water) was added, and the solution heated at 80°-85° C. for 4 hours 20 minutes (at this point, tlc and NMR of an aliquot indicated a 75/15/10 ratio of desired azide/isomeric azide/starting material). The reaction was cooled, poured into water, and extracted twice into ethyl acetate. The organic layer was washed with water and brine, dried over sodium sulfate and evaporated. The residue was chromatographed on silica gel using 3:1 hexane/ethyl acetate to give 5.80 grams (77%) of a foam which solidified.

出典