4-Amino-1-naphthalenesulfonic acid → 4-Methanesulfonamido-1-naphthalene sulfonic acid pyridinium salt

HRID 565801

Reaktionsgleichung

Reaktionsgleichung von HRID 565801
[NH2:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([S:12]([OH:15])(=[O:14])=[O:13])=[CH:4][CH:3]=1.[CH3:16][S:17](Cl)(=[O:19])=[O:18]>N1C=CC=CC=1>[NH+:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1.[CH3:16][S:17]([NH:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([S:12]([O-:15])(=[O:13])=[O:14])=[CH:4][CH:3]=1)(=[O:19])=[O:18]

Komponenten

4

Edukt 2

HCID 67904-Amino-1-naphthalenesulfonic acidHCID 31297Methanesulfonyl chloride

Produkt 1

HCID 1317221234-Methanesulfonamido-1-naphthalene sulfonic acid pyridinium saltAusbeute 123,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1049PyridineLösungsmittel

Versuchsvorschrift

A suspension of 4-amino-1-naphthalene sulfonic acid (200 g, 0.897 mole) in 800 ml of pyridine was stirred mechanically while methanesulfonyl chloride (70 ml, 0.9 mole) was added slowly over about 10 min. The reaction warmed to about 60° as the solid dissolved and then slowly cooled to room temperature. The mixture was stirred overnight while a solid precipitated. After filtering and washing with 500 ml of ether, the solid was dried under a nitrogen stream to afford 211 g (62%) of 4-methanesulfonamido-1-naphthalene sulfonic acid pyridinium salt.

Aufarbeitung

  1. additionwas added slowly over about 10 min
  2. temperatureThe reaction warmed to about 60° as the solid
  3. dissolutiondissolved
  4. customprecipitated
  5. filtrationAfter filtering
  6. washwashing with 500 ml of ether
  7. customthe solid was dried under a nitrogen stream

Quellen und Nachweise

ORD-Eintrag
ord-a153fc696dc3431189785507dd4ef025
Quelldatensatz
uspto-grants-2001_01
Patentnummer
US06172260B2

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