4-Vinylpyridine → HCID 54406405, compound

HRID 1605524Notes

Reaction equation

HRID 1605524 reaction equation
[SH: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].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>[O:11]([C:10]1[C:9]([S:18](=[O:21])(=[O:20])[NH2:19])=[CH:8][C:4]([C:5]([OH:7])=[O:6])=[CH:3][C:2]=1[S:1][CH2:36][CH2:35][C:37]1[CH:42]=[CH:41][N:40]=[CH:39][CH:38]=1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

6

Reactant 4

HCID 75024-VinylpyridineHCID 24489Sodium DithioniteHCID 516892Sodium Bicarbonate2×HCID 21520079HCID 21520079, compound

Product 1

HCID 54406405HCID 54406405, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of 3-mercapto-4-phenoxy-5-sulfamylbenzoic acid (1.7 g), sodium hydrogen carbonate (1 g), sodium dithionite (1 g), 4-vinylpyridine (0.8 ml) and saturated aqueous sodium hydrogen carbonate (17 ml) is stirred at 70° C. for 4 hours. After cooling, pH of the mixture is adjusted to 4.5 by addition of acetic acid. The precipitated material is collected by filtration, washed with water, and recrystallized from aqueous ethanol to yield 4-phenoxy-3-(4-pyridylethylthio)-5-sulfamylbenzoic acid.

Workup

  1. temperatureAfter cooling
  2. filtrationThe precipitated material is collected by filtration
  3. washwashed with water
  4. customrecrystallized from aqueous ethanol

Sources & evidence

ORD record
ord-3d3da97f052a4b0aab46bdbf61d258f4
Source dataset
uspto-grants-1976_04
Patent number
US03950376

Reaction notes

Loading…