Sodium Hydroxide → 3-Amino-4-phenoxy-5-sulfamoylbenzoic acid

HRID 1287766Notes

Reaction equation

HRID 1287766 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([S:18](=[O:21])(=[O:20])[NH2:19])[C:10]=1[O:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[C:5](N)=[O:6].[OH-:22].[Na+]>>[NH2:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([S:18](=[O:21])(=[O:20])[NH2:19])[C:10]=1[O:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[C:5]([OH:22])=[O:6]

Participants

3

Reactant 2

HCID 14798Sodium HydroxideHCID 215060743-Amino-4-phenoxy-5-sulphamyl-benzamide

Product 1

HCID 1199273-Amino-4-phenoxy-5-sulfamoylbenzoic acid

Procedure

A mixture of 3-amino-4-phenoxy-5-sulphamyl-benzamide (1 g) and 1N sodium hydroxide (20 ml) was refluxed for 1 hour. After cooling, the 3-amino-4-phenoxy-5-sulphamyl-benzoic acid was precipitated from the reaction mixture by addition of 4N hydrochloric acid until pH 2.5. After several recrystallizations from aqueous ethanol and drying, the compound was obtained with a melting point of 252°-253° C.

Workup

  1. temperaturewas refluxed for 1 hour
  2. temperatureAfter cooling
  3. customthe 3-amino-4-phenoxy-5-sulphamyl-benzoic acid was precipitated from the reaction mixture by addition of 4N hydrochloric acid until pH 2.5
  4. customAfter several recrystallizations from aqueous ethanol
  5. customdrying
  6. customthe compound was obtained with a melting point of 252°-253° C.

Sources & evidence

ORD record
ord-d702961650a44800b82e4cb81856fa38
Source dataset
uspto-grants-1976_10
Patent number
US03985777

Reaction notes

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