2-Cyano-4-methylpyridine → HCID 59750318, compound

HRID 499281Notes

Reaction equation

HRID 499281 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=O)=[C:4]([SH:11])[CH:3]=1.[C:12]([C:14]1[CH:19]=[C:18]([CH3:20])[CH:17]=[CH:16][N:15]=1)#[N:13]>N1C=CC=CC=1>[Cl:1][C:2]1[CH:10]=[CH:9][C:5]2[C:6](=[O:8])[N:13]=[C:12]([C:14]3[CH:19]=[C:18]([CH3:20])[CH:17]=[CH:16][N:15]=3)[S:11][C:4]=2[CH:3]=1

Participants

4

Reactant 2

HCID 887392-Cyano-4-methylpyridineHCID 204569744-Chloro-2-sulfanylbenzoic acid

Product 1

HCID 59750318HCID 59750318, compoundYield 32%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A mixture of 4-chloro-2-mercaptobenzoic acid (3.0 g, 15.9 mmol), 2-cyano-4-methylpyridine (1.9 g, 16.0 mmol) and pyridine (15 ml) was refluxed for 9 hrs as described in Example 9. After cooling, the precipitated crystals were collected by filtration, subjected to a silica gel column chromatography, eluted with ethyl acetate-methanol (5:1, v/v) and recrystallized from chlorobenzene-hexane to give the titled compound (1.47 g, 32%)

Workup

  1. temperaturewas refluxed for 9 hrs
  2. temperatureAfter cooling
  3. filtrationthe precipitated crystals were collected by filtration
  4. washeluted with ethyl acetate-methanol (5:1
  5. customv/v) and recrystallized from chlorobenzene-hexane

Sources & evidence

ORD record
ord-bf06e223a1df4f59928614f8cf27cb85
Source dataset
uspto-grants-2010_08
Patent number
US07767665B2

Reaction notes

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