4-Chloro-2-sulfanylbenzoic acid → HCID 22939347, compound

HRID 499446Notes

Reaction equation

HRID 499446 reaction equation
[C:1]([C:3]1[N:8]=[C:7]([CH2:9][CH2:10][C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH:6]=[C:5]([CH3:18])[CH:4]=1)#[N:2].[Cl:19][C:20]1[CH:21]=[C:22]([SH:29])[C:23](=[CH:27][CH:28]=1)[C:24](O)=[O:25]>N1C=CC=CC=1>[Cl:19][C:20]1[CH:28]=[CH:27][C:23]2[C:24](=[O:25])[N:2]=[C:1]([C:3]3[N:8]=[C:7]([CH2:9][CH2:10][C:11]([O:13][C:14]([CH3:15])([CH3:17])[CH3:16])=[O:12])[CH:6]=[C:5]([CH3:18])[CH:4]=3)[S:29][C:22]=2[CH:21]=1

Participants

4

Reactant 2

HCID 204569744-Chloro-2-sulfanylbenzoic acidHCID 22939494HCID 22939494, compound

Product 1

HCID 22939347HCID 22939347, compoundYield 28.3%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

tert-Butyl 3-(6-cyano-4-methyl-2-pyridyl)propanoate (0.69 g, 2.8 mmol) and 4-chlorothiosalicylic acid (1.05 g, 5.7 mmol) were dissolved in pyridine (10 ml). The mixture was refluxed for 22 hrs. The solvent was evaporated, and the residue was subjected to a silica gel column chromatography. The fractions eluted with hexane-ethyl acetate (3:1, v/v) were collected, concentrated and recrystallized from hexane-ethyl acetate to give the titled compound (0.33 g, 28%) as white crystals.

Workup

  1. temperatureThe mixture was refluxed for 22 hrs
  2. customThe solvent was evaporated
  3. washThe fractions eluted with hexane-ethyl acetate (3:1
  4. customv/v) were collected
  5. concentrationconcentrated
  6. customrecrystallized from hexane-ethyl acetate

Sources & evidence

ORD record
ord-1f59bcb4a9884cc696a2cb269ac26ff0
Source dataset
uspto-grants-2010_08
Patent number
US07767665B2

Reaction notes

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