Ethyl 3-benzylamino-5-methylsulphamyl-4-phenoxy-benzoate → 3-Benzylamino-5-methylsulphamyl-4-phenoxy-benzoic acid

HRID 918693Notes

Reaction equation

HRID 918693 reaction equation
[CH2:1]([NH:8][C:9]1[CH:10]=[C:11]([CH:17]=[C:18]([S:27](=[O:31])(=[O:30])[NH:28][CH3:29])[C:19]=1[O:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[C:12]([O:14]CC)=[O:13])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>[OH-].[Na+]>[CH2:1]([NH:8][C:9]1[CH:10]=[C:11]([CH:17]=[C:18]([S:27](=[O:31])(=[O:30])[NH:28][CH3:29])[C:19]=1[O:20][C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1)[C:12]([OH:14])=[O:13])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

3

Reactant 1

HCID 21506047Ethyl 3-benzylamino-5-methylsulphamyl-4-phenoxy-benzoate

Product 1

HCID 215060063-Benzylamino-5-methylsulphamyl-4-phenoxy-benzoic acid

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

Ethyl 3-benzylamino-5-methylsulphamyl-4-phenoxy-benzoate (0.5 g) was dissolved in 1N sodium hydroxide (8 ml) and heated on a steam bath for 1 hour. After cooling, the 3-benzylamino-5-methylsulphamyl-4-phenoxy-benzoic acid was precipitated by addition of 4N hydrochloric acid until a pH of 2.5. The precipitate was collected by suction and recrystallized from aqueous ethanol. After drying in vacuo, the melting point of the compound was 231-233°C.

Workup

  1. temperatureheated on a steam bath for 1 hour
  2. temperatureAfter cooling
  3. customthe 3-benzylamino-5-methylsulphamyl-4-phenoxy-benzoic acid was precipitated by addition of 4N hydrochloric acid until a pH of 2.5
  4. customThe precipitate was collected by suction
  5. customrecrystallized from aqueous ethanol
  6. customAfter drying in vacuo
  7. customwas 231-233°C.

Sources & evidence

ORD record
ord-d567f286d733455c96039db4c7e92bf8
Source dataset
uspto-grants-1976_07
Patent number
US03971819

Reaction notes

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