4-Nitrobenzenesulfonic acid → Nosyl ether

HRID 1252767

Reaction equation

HRID 1252767 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([S:10]([OH:13])(=[O:12])=[O:11])=[CH:6][CH:5]=1)([O-:3])=[O:2].O=P12OP3(OP(OP(O3)(O1)=O)(=O)O2)=O>ClC=CCl>[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([S:10]([O:13][S:10]([C:7]2[CH:6]=[CH:5][C:4]([N+:1]([O-:3])=[O:2])=[CH:9][CH:8]=2)(=[O:11])=[O:12])(=[O:11])=[O:12])=[CH:8][CH:9]=1)([O-:3])=[O:2]

Participants

4

Reactant 2

HCID 87404-Nitrobenzenesulfonic acidHCID 14812Phosphorus oxide (P4O10)

Product 1

HCID 13084338Nosyl etherYield 20.9%

Reagents, catalysts & solvents 1

HCID 109001,2-DichloroethyleneSolvent

Procedure

A mixture of p-nitrobenzensulfonic acid (20 g), phosphorous pentoxide (50 g) and 1,2-dichloroethylene (100 ml) is heated at reflux for 4 days. The hot supernatant is decanted from the gummy residue and allowed to cool to room temperature. The resulting crystalline precipitate of p-nitrobenzenesulfonic anhydride (1.5 g) is collected, washed with anhydrous diethylether, and dried under vacuum. The gummy residue is twice more refluxed overnight with 100 ml portions of dichloroethylene and worked up as above to provide additional p-nitrobenzenesulfonic anhydride (4.0 g); mp 171°-172°.

Workup

  1. temperatureis heated
  2. temperatureat reflux for 4 days
  3. customThe hot supernatant is decanted from the gummy residue
  4. customThe resulting crystalline precipitate of p-nitrobenzenesulfonic anhydride (1.5 g) is collected
  5. washwashed with anhydrous diethylether
  6. customdried under vacuum
  7. temperatureThe gummy residue is twice more refluxed overnight with 100 ml portions of dichloroethylene

Sources & evidence

ORD record
ord-a0f43e6085174fc7a9fb6bcda8e73089
Source dataset
uspto-grants-1988_05
Patent number
US04745188

Linked notes

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