2-Nitrobenzenesulfonyl chloride → o-Nitrobenzenesulfonyl Azide

HRID 1112034Notes

Reaction equation

HRID 1112034 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[S:10](Cl)(=[O:12])=[O:11])([O-:3])=[O:2].[N-:14]=[N+:15]=[N-:16].[Na+]>C(O)C.O>[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[S:10]([N:14]=[N+:15]=[N-:16])(=[O:12])=[O:11])([O-:3])=[O:2]

Participants

5

Reactant 2

HCID 155402-Nitrobenzenesulfonyl chlorideHCID 33557Sodium Azide

Product 1

HCID 5123252o-Nitrobenzenesulfonyl AzideYield 92%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a solution of 15.0 g (0.069 mole) of o-nitrobenzenesulfonyl chloride dissolved in 150 ml ethanol was added 5.89 g (0.090 mole) of sodium azide dissolved in a minimum amount of water. The solution was stirred for 30 minutes and then poured into a 2 liter Erlenmeyer flask containing 500 ml of ice water. The resultant white solid was filtered, dried and recrystallized from ethanol. The purified product had a melting point 73°-74° C. (lit. 73°-74° C.) and was isolated in 92% yield (14.47 g).

Workup

  1. additionpoured into a 2 liter Erlenmeyer flask
  2. filtrationThe resultant white solid was filtered
  3. customdried
  4. customrecrystallized from ethanol
  5. customa melting point 73°-74° C. (lit. 73°-74° C.)
  6. customwas isolated in 92% yield (14.47 g)

Sources & evidence

ORD record
ord-1433ce600ba74d748290672e5c1360df
Source dataset
uspto-grants-1978_10
Patent number
US04120652

Reaction notes

Loading…