4-Methyl-2-sulfanylbenzoic acid → HCID 22939357, compound

HRID 499422Notes

Reaction equation

HRID 499422 reaction equation
[SH:1][C:2]1[CH:10]=[C:9]([CH3:11])[CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=O.[C:12]([C:14]1[N:19]=[C:18]([CH2:20][CH2:21][C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH:17]=[CH:16][CH:15]=1)#[N:13]>N1C=CC=CC=1>[CH3:11][C:9]1[CH:8]=[CH:7][C:3]2[C:4](=[O:6])[N:13]=[C:12]([C:14]3[N:19]=[C:18]([CH2:20][CH2:21][C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH:17]=[CH:16][CH:15]=3)[S:1][C:2]=2[CH:10]=1

Participants

4

Reactant 2

HCID 200954184-Methyl-2-sulfanylbenzoic acidHCID 22939301Tert-butyl 3-(6-cyano-2-pyridyl)propanoate

Product 1

HCID 22939357HCID 22939357, compoundYield 53.5%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

2-Mercapto-4-methylbenzoic acid (1.56 g, 9.3 mmol) and tert-butyl 3-(6-cyano-2-pyridyl)propanoate (1.46 g, 6.3 mmol) were dissolved in pyridine (15 ml), and the mixture was refluxed for 6 hrs. The reaction mixture was concentrated under reduced pressure, subjected to silica gel column chromatography, eluted with hexane-ethyl acetate (3:2, v/v) and recrystallized from ethyl acetate-hexane to give the titled compound (1.29 g, 53%).

Workup

  1. temperaturethe mixture was refluxed for 6 hrs
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. washeluted with hexane-ethyl acetate (3:2
  4. customv/v) and recrystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-a2f2c57bcad44da7b127be17819761b8
Source dataset
uspto-grants-2010_08
Patent number
US07767665B2

Reaction notes

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