Sodium Hydroxide → 1-Azidostyrene

26.4 g of 1,2-dibromostyrene was dissolved in 150 ml of dimethylsulfoxide, then 9.8 g of sodium azide was added little by little at 15° to 18° C. in an atmosphere of nitrogen, and the mixture was stirred at room temperature for 10 hours. Then the reaction mixture was cooled to 10° C. and 10 g of a 50% aqueous sodium hydroxide solution was added dropwise thereto. After the addition the reaction mixture was stirred for 24 hours at room temperature, then 400 ml of a 2% aqueous sodium hydrogencarbonate solution was poured to it, and extraction with 150 ml of methylene chloride was carried out. After drying the extract liquid the solvent was distilled off under reduced pressure. 50 ml of n-hexane was added to the residue and the solution was treated by simple column chromatography, wherein the column was filled with 50 g of alumina (eluent: n-hexane). The solvent was removed from the elutant by distillation under reduced pressure, to obtain 14.4 g of 1-azidostyrene (B).

1. temperatureThen the reaction mixture was cooled to 10° C.
2. additionAfter the addition the reaction mixture
3. stirringwas stirred for 24 hours at room temperature
4. customAfter drying the extract liquid the solvent
5. distillationwas distilled off under reduced pressure
6. addition50 ml of n-hexane was added to the residue
7. additionthe solution was treated by simple column chromatography, wherein the column
8. additionwas filled with 50 g of alumina (eluent: n-hexane)
9. customThe solvent was removed from the elutant by distillation under reduced pressure

ORD record

ord-36e383c79b5c4d62a489eb1ee126e0b1

Source dataset

uspto-grants-1993_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05260181