Ethanol → Ethyl 3-(ethylamino)-4-phenoxy-5-sulfamoylbenzoate

HRID 1287786Notes

Reaction equation

HRID 1287786 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]([OH:7])=[O:6].[CH2:22](I)[CH3:23].[CH2:25](O)[CH3:26]>>[CH2:25]([NH: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]([O:7][CH2:22][CH3:23])=[O:6])[CH3:26]

Participants

4

Reactant 3

HCID 702EthanolHCID 6340IodoethaneHCID 1199273-Amino-4-phenoxy-5-sulfamoylbenzoic acid

Product 1

HCID 21506140Ethyl 3-(ethylamino)-4-phenoxy-5-sulfamoylbenzoate

Procedure

A mixture of 3-amino-4-phenoxy-5-sulphamyl-benzoic acid (3.08 g), ethyl iodide (20 ml), and ethanol (20 ml) was refluxed for 6 days. After cooling, the reaction mixture was evaporated to dryness, and the residue was washed with a little ethanol followed by diethyl ether. The ethyl 3-ethylamino-4-phenoxy-5-sulphamyl-benzoate obtained was dissolved in 1N sodium hydroxide (35 ml) and heated on a steam bath for 30 minutes. After cooling, the reaction mixture was adjusted to pH 2.5 by addition of 4N hydrochloric acid, and the precipitated 3-ethylamino-4-phenoxy-5-sulphamyl-benzoic acid was isolated by filtration. After recrystallization from ethanol and drying in vacuo at 115° C, the compound was obtained with a melting point of 236°-237° C.

Workup

  1. temperaturewas refluxed for 6 days
  2. temperatureAfter cooling
  3. customthe reaction mixture was evaporated to dryness
  4. washthe residue was washed with a little ethanol

Sources & evidence

ORD record
ord-b6a70b68ad6c47a9a925c658bb4883f5
Source dataset
uspto-grants-1976_10
Patent number
US03985777

Reaction notes

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