تفاعل #81407

معادلة التفاعل

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

المردود 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

المردود 80.1%

المذيبات

water

water

ظروف التفاعل

المعالجة

1. 1
   أخرىTo a 125 ml round-bottomed flask equipped with a nitrogen inlet
2. 2
   workup.DISSOLUTIONAfter dissolution
3. 3
   درجة الحرارةthe solution heated at 80°-85° C. for 4 hours 20 minutes (at this point, tlc and NMR of an aliquot
4. 4
   درجة الحرارةThe reaction was cooled
5. 5
   استخلاصextracted twice into ethyl acetate
6. 6
   غسيلThe organic layer was washed with water and brine
7. 7
   تجفيفdried over sodium sulfate
8. 8
   أخرىevaporated
9. 9
   أخرىThe residue was chromatographed on silica gel using 3:1 hexane/ethyl acetate

الإجراء التجريبي

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.

المصدر