Hydrochloric Acid → N-(5-Hydroxy-6-sulfamoylnaphthalen-1-yl)acetamide

HRID 1579949

Reaction equation

HRID 1579949 reaction equation
[C:1]([NH:4][C:5]1[CH:14]=[CH:13][CH:12]=[C:11]2[C:6]=1[CH:7]=[CH:8][C:9]([S:19](Cl)(=[O:21])=[O:20])=[C:10]2[O:15]C(=O)C)(=[O:3])[CH3:2].C(Cl)(Cl)Cl.C(=O)([O-])[O-].[NH4+:31].[NH4+].Cl>O>[C:1]([NH:4][C:5]1[CH:14]=[CH:13][CH:12]=[C:11]2[C:6]=1[CH:7]=[CH:8][C:9]([S:19]([NH2:31])(=[O:21])=[O:20])=[C:10]2[OH:15])(=[O:3])[CH3:2]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6212ChloroformHCID 941252-Naphthalenesulfonyl chloride, 5-(acetylamino)-1-(acetyloxy)-HCID 517111Ammonium Carbonate

Product 1

HCID 21486282N-(5-Hydroxy-6-sulfamoylnaphthalen-1-yl)acetamide

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

The 5-acetamido-1-hydroxynaphthalene-2-sulfonamide was prepared by dissolving 10.8 g. of 5-acetamido-1-acetoxynaphthalene-2-sulfonyl chloride in 10 ml. dry chloroform and heating on the steam bath with 25.0 g. anhydrous ammonium carbonate for 2.5 hours. The yellow-brown solid was dissolved by heating with 50 ml. water on the steam bath for 4 hours. Acidification with dilute hydrochloric acid to pH5 caused the sulfonamide to precipitate. It was filtered off, washed and dried, yielding 5.61 g. (63%).

Workup

  1. dissolutionby dissolving 10.8 g
  2. dissolutionThe yellow-brown solid was dissolved
  3. temperatureby heating with 50 ml
  4. customto precipitate
  5. filtrationIt was filtered off
  6. washwashed
  7. customdried
  8. customyielding 5.61 g

Sources & evidence

ORD record
ord-61010f5867524eb4bbd5b94f8f727856
Source dataset
uspto-grants-1976_01
Patent number
US03932380

Linked notes

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