Hydrochloric Acid → Benzmetanide

HRID 1287804Notes

Reaction equation

HRID 1287804 reaction equation
C([NH:4][S:5]([C:8]1[C:9]([O:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)=[C:10]([NH:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH:11]=[C:12]([CH:16]=1)[C:13]([OH:15])=[O:14])(=[O:7])=[O:6])(=O)C.Cl.[OH-].[Na+]>C(O)C>[CH2:18]([NH:17][C:10]1[CH:11]=[C:12]([CH:16]=[C:8]([S:5](=[O:7])(=[O:6])[NH2:4])[C:9]=1[O:25][C:26]1[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=1)[C:13]([OH:15])=[O:14])[C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1

Participants

5

Reactant 3

HCID 313Hydrochloric Acid2×HCID 14798Sodium HydroxideHCID 21506093HCID 21506093, compound

Product 1

HCID 168795Benzmetanide

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 5-acetylsulphamyl-3-benzylamino-4-phenoxy-benzoic acid (1 g), ethanol (20 ml), and 4N hydrochloric acid (5ml) was refluxed for 2.5 hours. Then 2N sodium hydroxide (15 ml) was added, and the reaction mixture was heated on a steam bath for 30 minutes. After cooling, the pH was adjusted to 2.5 by addition of 4N hydrochloric acid, and the precipitated 3-benzylamino-4-phenoxy-5-sulphamyl-benzoic acid was isolated by filtation. After recrystallization from aqueous ethanol and drying, the compound was obtained with a melting point of 264°-265° C.

Workup

  1. temperaturewas refluxed for 2.5 hours
  2. temperaturethe reaction mixture was heated on a steam bath for 30 minutes
  3. temperatureAfter cooling

Sources & evidence

ORD record
ord-f0e84e9918b6435689a3430b7949f827
Source dataset
uspto-grants-1976_10
Patent number
US03985777

Reaction notes

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