Phenethylamine → 3-Nitro-4-(beta-phenylethylamino)5-sulphamyl-benzoic acid

HRID 918625Notes

Reaction equation

HRID 918625 reaction equation
Cl[C:2]1[C:10]([S:11](=[O:14])(=[O:13])[NH2:12])=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][C:3]=1[N+:15]([O-:17])=[O:16].[C:18]1([CH2:24][CH2:25][NH2:26])[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>O>[N+:15]([C:3]1[CH:4]=[C:5]([CH:9]=[C:10]([S:11](=[O:14])(=[O:13])[NH2:12])[C:2]=1[NH:26][CH2:25][CH2:24][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[C:6]([OH:8])=[O:7])([O-:17])=[O:16]

Participants

4

Reactant 2

HCID 1001PhenethylamineHCID 898934-Chloro-3-nitro-5-sulphamoylbenzoic acid

Product 1

HCID 125913963-Nitro-4-(beta-phenylethylamino)5-sulphamyl-benzoic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 4-chloro-3-nitro-5-sulphamyl-benzoic acid (22.4 g), β-phenylethylamine (29 g), and water (200 ml) was refluxed for 2.5 hours. After cooling, the reaction mixture was adjusted to a pH of 9.5 and extracted with diethyl ether. The aqueous layer was then acidified by addition of 4N hydrochloric acid, and the precipitated 3-nitro-4-(β-phenylethylamino)-5-sulphamyl-benzoic acid was collected by suction. After recrystallization from aqueous ethanol, the melting point was 208°-208.5°C.

Workup

  1. temperaturewas refluxed for 2.5 hours
  2. temperatureAfter cooling
  3. extractionextracted with diethyl ether
  4. additionThe aqueous layer was then acidified by addition of 4N hydrochloric acid
  5. customthe precipitated 3-nitro-4-(β-phenylethylamino)-5-sulphamyl-benzoic acid was collected by suction
  6. customAfter recrystallization from aqueous ethanol

Sources & evidence

ORD record
ord-a7e4db9128a8439188d4805974fcb30d
Source dataset
uspto-grants-1976_07
Patent number
US03971819

Reaction notes

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