Acetic Acid → 4-Phenyl-3-(4-pyridylethylamino)-5-sulfamylbenzoic acid

HRID 1605579Notes

Reaction equation

HRID 1605579 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([S:17](=[O:20])(=[O:19])[NH2:18])[C:10]=1[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[C:5]([OH:7])=[O:6].[CH:21]([C:23]1[CH:28]=[CH:27][N:26]=[CH:25][CH:24]=1)=[CH2:22].C(O)(=O)C>CO.O>[C:11]1([C:10]2[C:9]([S:17](=[O:20])(=[O:19])[NH2:18])=[CH:8][C:4]([C:5]([OH:7])=[O:6])=[CH:3][C:2]=2[NH:1][CH2:22][CH2:21][C:23]2[CH:28]=[CH:27][N:26]=[CH:25][CH:24]=2)[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 75024-VinylpyridineHCID 215468413-Amino-4-phenyl-5-sulfamylbenzoic acid

Product 1

HCID 867332354-Phenyl-3-(4-pyridylethylamino)-5-sulfamylbenzoic acid

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A solution of 3-amino-4-phenyl-5-sulfamylbenzoic acid (1.46 g), 4-vinylpyridine (1.0 ml) and acetic acid (0.5 ml) in methanol (7.5 ml) is refluxed for 5-6 hours. After cooling, the resulting solution is diluted with water (16 ml) to precipitate crude 4-phenyl-3-(4-pyridylethylamino)-5-sulfamylbenzoic acid, which is collected by filtration, washed with water and dried. After recrystallization twice from aqueous ethanol, the acid is obtained with a melting point of 216.5°-217.5° C.

Workup

  1. temperatureAfter cooling
  2. customto precipitate crude 4-phenyl-3-(4-pyridylethylamino)-5-sulfamylbenzoic acid, which
  3. filtrationis collected by filtration
  4. washwashed with water
  5. customdried
  6. customAfter recrystallization twice from aqueous ethanol
  7. customthe acid is obtained with a melting point of 216.5°-217.5° C.

Sources & evidence

ORD record
ord-3fe73c39f5294b31a52fb73676dc65f9
Source dataset
uspto-grants-1976_04
Patent number
US03950380

Reaction notes

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