4-Nitrobenzenesulfonic acid → Nosyl ether

HRID 371287

Reaktionsgleichung

Reaktionsgleichung von HRID 371287
[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): mp 171°-172° C.

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-28fe738b1313463782ca4301b7cb768a
Quelldatensatz
uspto-grants-1985_07
Patentnummer
US04530841

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