HCID 18414578, compound → HCID 11501515, compound

HRID 991548Notes

Reaction equation

HRID 991548 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([C:10](=[O:29])[CH:11]([NH:18][C:19](=O)[C:20]3[CH:25]=[CH:24][C:23]([C:26]#[N:27])=[CH:22][CH:21]=3)[C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][N:13]=3)=[CH:9][C:4]=2[O:3][CH2:2]1>S(Cl)(Cl)=O>[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([C:10]3[O:29][C:19]([C:20]4[CH:21]=[CH:22][C:23]([C:26]#[N:27])=[CH:24][CH:25]=4)=[N:18][C:11]=3[C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][N:13]=3)=[CH:9][C:4]=2[O:3][CH2:2]1

Participants

3

Reactant 1

HCID 18414578HCID 18414578, compound

Product 1

HCID 11501515HCID 11501515, compoundYield 9.4%

Reagents, catalysts & solvents 1

HCID 24386Thionyl ChlorideSolvent

Procedure

N-(2-Benzo[1,3]dioxol-5-yl-2-oxo-1-pyridin-2-yl-ethyl)4-cyano-benzamide (0.1 g, 0.26 mmol) was dissolved in neat thionyl chloride (10 ml) and heated at reflux temperature for 2 hours. The cooled solution was cautiously added dropwise to a concentrated sodium hydroxide-ice mixture. The crude product was extracted into dichloromethane and purified using hexane-ethylacetate (1:1) as eluent to give the title compound (9 mg, 9%). 1H NMR (CDCl3) δ: 6.06 (2H, s), 6.84-6.99 (2H, m), 7.27-7.31 (1H, m), 7.86 (2H, d, J=7 Hz), 8.00 (2H, d, J=7 Hz), 8.04 (1H, s), 8.23 (1H, dd, J=7 and 1 Hz), 8.42 (1H, d, J=7 Hz), 8.65 (1H, dd, J=7 and 1 Hz); m/z (API) 368 (M+H+).

Workup

  1. temperatureheated
  2. temperatureat reflux temperature for 2 hours
  3. extractionThe crude product was extracted into dichloromethane
  4. custompurified

Sources & evidence

ORD record
ord-ab6c2575b5a5495f8bd43cd1136ec2b3
Source dataset
uspto-grants-2002_10
Patent number
US06465493B1

Reaction notes

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