4-Methoxybenzenesulfonyl chloride → 4547-64-2
Reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([S:9](Cl)(=[O:11])=[O:10])=[CH:5][CH:4]=1.[N-:13]=[N+:14]=[N-:15].[Na+].S(Cl)(Cl)(=O)=O>C(O)C.O>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([S:9]([N:13]=[N+:14]=[N-:15])(=[O:11])=[O:10])=[CH:5][CH:4]=1Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 30 °C
Procedure
274 g (1.33 mole) of p-methoxybenzenesulfonyl chloride was dissolved in one liter ethanol in a two liter Erlenmeyer flask. The solution was stirred magnetically and warmed to 30° C. 112 g (1.72 mole) of sodium azide was dissolved in a minimum amount of water and the sodium azide solution was then added to the sulfonyl chloride solution. Sodium chloride precipitated over a 30 minute period. The reaction solution was then poured into a 4 liter Erlenmeyer flask containing 2 liters of ice water. The resultant white solid was removed by filtration and air dried in a vacuum oven overnight at room temperature; yield 281 g of p-methoxybenzenesulfonyl azide (99% of theory; mp 39°-42° C.). The sample was crystallized from methanol to yield a white solid in 96% yield, mp 48°-50° C., lit. value mp 52° C.
Workup
- customSodium chloride precipitated over a 30 minute period
- additionThe reaction solution was then poured into a 4 liter Erlenmeyer flask
- additioncontaining 2 liters of ice water
- customThe resultant white solid was removed by filtration and air
- customdried in a vacuum oven overnight at room temperature
- customThe sample was crystallized from methanol
- customto yield a white solid in 96% yield, mp 48°-50° C., lit. value mp 52° C.
Sources & evidence
- ORD record
- ord-531cfb83e65646c1924c308e28c32fb8
- Source dataset
- uspto-grants-1978_10
- Patent number
- US04120652
Reaction notes
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