4-Vinylpyridine → HCID 53991723, compound

HRID 328968Notes

Reaction equation

HRID 328968 reaction equation
[CH2:1]([C:8]1[C:16]([S:17](=[O:20])(=[O:19])[NH2:18])=[CH:15][C:11]([C:12]([OH:14])=[O:13])=[CH:10][C:9]=1[SH:21])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(=O)([O-])O.[Na+].S(S([O-])=O)([O-])=O.[Na+].[Na+].[CH:35]([C:37]1[CH:42]=[CH:41][N:40]=[CH:39][CH:38]=1)=[CH2:36]>C(O)(=O)C>[CH2:1]([C:8]1[C:16]([S:17](=[O:20])(=[O:19])[NH2:18])=[CH:15][C:11]([C:12]([OH:14])=[O:13])=[CH:10][C:9]=1[S:21][CH2:36][CH2:35][C:37]1[CH:42]=[CH:41][N:40]=[CH:39][CH:38]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 75024-VinylpyridineHCID 24489Sodium DithioniteHCID 516892Sodium Bicarbonate2×HCID 21440227HCID 21440227, compound

Product 1

HCID 53991723HCID 53991723, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of 4-benzyl-3-mercapto-5-sulfamylbenzoic acid (3.25 g), sodium hydrogen carbonate (2.0 g), sodium dithionite (2.0 g), 4-vinylpyridine (1.5 ml) and saturated sodium hydrogen carbonate (33 ml) is stirred at 70° C. for 4 hours. After cooling, the mixture is acidified with 4 N acetic acid. The separated material is collected by filtration and washed with water. After drying and recrystallization twice from aqueous ethanol, 4-benzyl-3-(4-pyridylethylthio)-5-sulfamylbenzoic acid is obtained as a hemihydrate with a melting point of 180° -182° C..

Workup

  1. temperatureAfter cooling
  2. filtrationThe separated material is collected by filtration
  3. washwashed with water
  4. customAfter drying
  5. customrecrystallization twice from aqueous ethanol

Sources & evidence

ORD record
ord-d66ce5c715a04e399c7d24510f86f438
Source dataset
uspto-grants-1977_04
Patent number
US04018794

Reaction notes

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