4-Nitrobenzenesulfonic acid → Nosyl ether

HRID 247494

Reaktionsgleichung

Reaktionsgleichung von HRID 247494
[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]

Komponenten

4

Edukt 2

HCID 87404-Nitrobenzenesulfonic acidHCID 14812Phosphorus oxide (P4O10)

Produkt 1

HCID 13084338Nosyl etherAusbeute 20,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 109001,2-DichloroethyleneLösungsmittel

Versuchsvorschrift

A mixture of p-nitrobenzenesulfonic 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) m.p. 171°-172°.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-6f9d47e5ee374636951a3aca2c14ee78
Quelldatensatz
uspto-grants-1987_11
Patentnummer
US04707547

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