4-Chloro-2-sulfanylbenzoic acid → HCID 59750211, compound

HRID 748338Notes

Reaction equation

HRID 748338 reaction equation
[C:1]([C:3]1[CH:8]=[C:7]([CH2:9][CH2:10][P:11](=[O:18])([O:15][CH2:16][CH3:17])[O:12][CH2:13][CH3:14])[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][P:11](=[O:18])([O:12][CH2:13][CH3:14])[O:15][CH2:16][CH3:17])[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 22939314HCID 22939314, compound

Product 1

HCID 59750211HCID 59750211, compoundYield 15.3%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Diethyl 2-(2-cyano-4-pyridyl)ethylphosphonate (1.7 g, 6.4 mmol) and 4-chlorothiosalicylic acid (2.4 g, 12.8 mmol) were dissolved in pyridine (30 ml), and the mixture was refluxed for 13 hrs. The solvent was evaporated, and the residue was subjected to a silica gel column chromatography. The fractions eluted with ethyl acetate-chloroform (1:1, v/v) were collected, concentrated and recrystallized from hexane-tetrahydrofuran to give the titled compound (0.43 g, 15%) as white crystals.

Workup

  1. temperaturethe mixture was refluxed for 13 hrs
  2. customThe solvent was evaporated
  3. washThe fractions eluted with ethyl acetate-chloroform (1:1
  4. customv/v) were collected
  5. concentrationconcentrated
  6. customrecrystallized from hexane-tetrahydrofuran

Sources & evidence

ORD record
ord-36755dfee47e4933b4b0c4092cf91c6d
Source dataset
uspto-grants-2008_07
Patent number
US07399759B2

Reaction notes

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