Reacción #81407

Ecuación de reacción

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

Rendimiento 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

Rendimiento 80.1%

Disolventes

water

water

Condiciones de reacción

Tratamiento posterior

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

Procedimiento

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.

Fuente