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Lithium Hydroxide → 2,6-bis(3-cyanophenoxy)-N-methylpyridine-4-carboxamide

HRID 1418407
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1418407
[C:1]([C:3]1[CH:4]=[C:5]([CH:27]=[CH:28][CH:29]=1)[O:6][C:7]1[CH:12]=[C:11]([C:13](OCC)=[O:14])[CH:10]=[C:9]([O:18][C:19]2[CH:24]=[CH:23][CH:22]=[C:21]([C:25]#[N:26])[CH:20]=2)[N:8]=1)#[N:2].[OH-].[Li+].S(Cl)(Cl)=O.Cl.[CH3:37][NH2:38].C(=O)([O-])[O-].[K+].[K+]>O1CCCC1.O>[C:1]([C:3]1[CH:4]=[C:5]([CH:27]=[CH:28][CH:29]=1)[O:6][C:7]1[CH:12]=[C:11]([C:13]([NH:38][CH3:37])=[O:14])[CH:10]=[C:9]([O:18][C:19]2[CH:24]=[CH:23][CH:22]=[C:21]([C:25]#[N:26])[CH:20]=2)[N:8]=1)#[N:2]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 5

HCID 3939Lithium HydroxideHCID 11430Potassium CarbonateHCID 24386Thionyl ChlorideHCID 6364545Methylamine hydrochlorideHCID 10833960HCID 10833960, Verbindung

Produkt 1

HCID 104993832,6-bis(3-cyanophenoxy)-N-methylpyridine-4-carboxamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 21881883Oxolane--water (1/1)Lösungsmittel

Versuchsvorschrift

To 2,6-bis(3-cyanophenoxy)pyridine-4-carboxylic acid, ethyl ester (1.6 g, 4.0 mmol) in tetrahydrofuran/water (50 mL, 1/1) was added lithium hydroxide (0.85 g, 20 mmol). After stirring for 1.5 hours the reaction was partitioned with 1M HCl and ethyl acetate. The organic layer was separated, dried (MgSO4), and the solvent was removed in vacuo. The residue was dissolved in methylene chloride (50 mL) and thionyl chloride (2.4 g, 20 mmol) was added. After stirring for 2 hours the solvent was removed in vacuo. The residue was dissolved in methylene chloride/water (30/10 mL) and methylamine hydrochloride (0.090 g, 1.3 mmol) and potassium carbonate (0.46 g, 3.3 mmol) were added. The organic layer was separated, washed with brine, dried (MgSO4), and the solvent removed in vacuo to give 2,6-bis(3-cyanophenoxy)-N-methylpyridine-4-carboxamide; NMR (CDCl3) 7.5 (m,4), 7.3 (m,4), 7.0 (s,2), 6.25 (br s,1), 3.1 (d,3) ppm.

Aufarbeitung

  1. customwas partitioned with 1M HCl and ethyl acetate
  2. customThe organic layer was separated
  3. dry with materialdried (MgSO4)
  4. customthe solvent was removed in vacuo
  5. dissolutionThe residue was dissolved in methylene chloride (50 mL)
  6. stirringAfter stirring for 2 hours the solvent
  7. customwas removed in vacuo
  8. dissolutionThe residue was dissolved in methylene chloride/water (30/10 mL)
  9. customThe organic layer was separated
  10. washwashed with brine
  11. dry with materialdried (MgSO4)
  12. customthe solvent removed in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-249598f9c9454aebbea80f45647b3872
Quelldatensatz
uspto-grants-1999_03
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05883100

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