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

HRID 565800

Reaction equation

HRID 565800 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 600 as the solid dissolved and then slowly cooled to rt. 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 600 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-e5c7fb17fb9a464694b5c0e230afb5f5
Source dataset
uspto-grants-2001_01
Patent number
US06172260B2

Linked notes

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