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

HRID 1287737Notes

Reaction equation

HRID 1287737 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-b4378081c6b04b51be8340043309b864
Source dataset
uspto-grants-1976_10
Patent number
US03985777

Reaction notes

Loading…