4-Chloro-2-sulfanylbenzoic acid → HCID 22939577, compound

HRID 499432Notes

Reaction equation

HRID 499432 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([SH:11])[C:5](=[CH:9][CH:10]=1)[C:6]([OH:8])=O.[C:12]([C:14]1[CH: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][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]([CH2:20][CH2:21][C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH:17]=[CH:16][N:15]=3)[S:11][C:4]=2[CH:3]=1

Participants

4

Reactant 2

HCID 204569744-Chloro-2-sulfanylbenzoic acidHCID 22939349HCID 22939349, compound

Product 1

HCID 22939577HCID 22939577, compoundYield 53.8%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

4-Chlorothiosalicylic acid (2.3 g, 12.2 mmol) and tert-butyl 3-(2-cyano-4-pyridyl)propanoate (1.4 g, 6.0 mmol) were dissolved in pyridine (20 ml), and the mixture was refluxed for 16 hrs. The solvent was evaporated and the residue was subjected to a silica gel column chromatography. The fraction eluted with hexane-ethyl acetate (2:1, v/v) were collected, concentrated and recrystallized from hexane-tetrahydrofuran to give the titled compound (1.3 g, 52%) as white crystals.

Workup

  1. temperaturethe mixture was refluxed for 16 hrs
  2. customThe solvent was evaporated
  3. washThe fraction eluted with hexane-ethyl acetate (2:1
  4. customv/v) were collected
  5. concentrationconcentrated
  6. customrecrystallized from hexane-tetrahydrofuran

Sources & evidence

ORD record
ord-3a018c05857e4a3fbf4f0a0a055b992f
Source dataset
uspto-grants-2010_08
Patent number
US07767665B2

Reaction notes

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