Dimethylcarbamoyl Chloride → 4-Isopropylpicolinonitrile

HRID 2070924Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2070924
[CH:1]([C:4]1[CH:9]=[CH:8][N+:7]([O-])=[CH:6][CH:5]=1)([CH3:3])[CH3:2].[Si]([C:15]#[N:16])(C)(C)C.CN(C)C(Cl)=O>C(Cl)Cl.C(Cl)(Cl)Cl>[CH:1]([C:4]1[CH:9]=[CH:8][N:7]=[C:6]([C:15]#[N:16])[CH:5]=1)([CH3:3])[CH3:2]

Komponenten

6

Edukt 3

HCID 6598Dimethylcarbamoyl ChlorideHCID 82115Trimethylsilyl cyanideHCID 3156064-Isopropyl-pyridine 1-oxide

Produkt 1

HCID 450794854-Isopropylpicolinonitrile

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6212ChloroformLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a stirring solution of 139 mg (1.01 mmol) of 4-isopropylpyridine N-oxide in 10 mL of CH2Cl2 at r.t. was added 160 μL (1.20 mmol) of TMSCN. After 5 min., 100 μL (1.09 mmol) of dimethylcarbamyl chloride was added, and the solution was stirred at r.t. for 16 h. The solution was diluted with chloroform and washed with 20 mL of 10% aqueous K2CO3. The layers were separated, and the aqueous layer was extracted 3 times with CHCl3. The combined extracts were dried over Na2SO4, filtered, and concentrated. Purification by flash silica gel chromatography (30% EtOAc/hexanes) provided 4-isopropylpicolinonitrile with some impurity as a liquid.

Aufarbeitung

  1. washwashed with 20 mL of 10% aqueous K2CO3
  2. customThe layers were separated
  3. extractionthe aqueous layer was extracted 3 times with CHCl3
  4. dry with materialThe combined extracts were dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customPurification by flash silica gel chromatography (30% EtOAc/hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-57fa147eeac14ca19f137fae5cf20232
Quelldatensatz
uspto-grants-2012_10
Patentnummer
US08299267B2

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