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4-Vinylpyridine → HCID 54406405, compound

HRID 1605524
Notes
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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
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

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 176
Acetic Acid
Solvent

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
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US03950376

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes