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

HRID 565801

Reaction equation

HRID 565801 reaction equation
[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]

Participants

4

Reactant 2

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

Product 1

HCID 1317221234-Methanesulfonamido-1-naphthalene sulfonic acid pyridinium saltYield 123.7%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-a153fc696dc3431189785507dd4ef025
Source dataset
uspto-grants-2001_01
Patent number
US06172260B2

Linked notes

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