4-Chloro-2-sulfanylbenzoic acid → HCID 22939621, compound

HRID 499488Notes

Reaction equation

HRID 499488 reaction equation
[C:1]([C:3]1[CH:8]=[C:7]([CH2:9][CH2:10][NH:11][C:12](=[O:18])[O:13][C:14]([CH3:17])([CH3:16])[CH3:15])[CH:6]=[CH:5][N: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[CH:8]=[C:7]([CH2:9][CH2:10][NH:11][C:12](=[O:18])[O:13][C:14]([CH3:15])([CH3:17])[CH3:16])[CH:6]=[CH:5][N:4]=3)[S:29][C:22]=2[CH:21]=1

Participants

4

Reactant 2

HCID 204569744-Chloro-2-sulfanylbenzoic acidHCID 22939273HCID 22939273, compound

Product 1

HCID 22939621HCID 22939621, compoundYield 19.1%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

tert-Butyl 2-(2-cyano-4-pyridyl)ethylcarbamate (1.5 g, 6.0 mmol) and 4-chlorothiosalicylic acid (2.3 g, 12.1 mmol) were dissolved in pyridine (10 ml), and the mixture was refluxed for 18 hrs. The solvent was evaporated, and the residue was subjected to a silica gel column chromatography. The fractions eluted with hexane-ethyl acetate (1:1, v/v) were collected, concentrated and recrystallized from hexane-tetrahydrofuran to give the titled compound (0.48 g, 19%) as white crystals.

Workup

  1. temperaturethe mixture was refluxed for 18 hrs
  2. customThe solvent was evaporated
  3. washThe fractions eluted with hexane-ethyl acetate (1:1
  4. customv/v) were collected
  5. concentrationconcentrated
  6. customrecrystallized from hexane-tetrahydrofuran

Sources & evidence

ORD record
ord-e6d9d706ce9442e89634ca7c0a95a1b9
Source dataset
uspto-grants-2010_08
Patent number
US07767665B2

Reaction notes

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