Dimethylformamide → HCID 86664842, Verbindung

HRID 2365237Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2365237
[CH3:1][N:2]1[CH:6]=[C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][N:8]=2)[N:4]=[N:3]1.[Li]CCCC.CN([CH:21]=[O:22])C.[Cl-].[NH4+]>C1COCC1>[CH3:1][N:2]1[C:6]([CH:21]=[O:22])=[C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][N:8]=2)[N:4]=[N:3]1

Komponenten

6

Edukt 4

HCID 6228DimethylformamideHCID 25517Ammonium ChlorideHCID 57746172HCID 57746172, VerbindungHCID 178418339Butyllithium

Produkt 1

HCID 86664842HCID 86664842, VerbindungAusbeute 91 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
-75 °C

Versuchsvorschrift

To a solution of 2-(1-methyl-1H-[1,2,3]triazol-4-yl)-pyridine (3.52 g, 22 mmol) in THF (112 mL) was added n-BuLi (1.6 M in hexane, 16.5 mL, 4.96 mmol) dropwise at −75° C. and under Ar. The resulted light brown suspension was stirred at −75° C. for 1 h. Then DMF (2.20 mL, 29 mmol) was added dropwise at −75° C. and the yellow solution was allowed to warm up to room temperature over 1 h. The mixture was then poured into saturated ammonium chloride solution and extracted with ethyl acetate and the combined organic extracts washed with brine, dried over sodium sulphate, filtered and evaporated. Purification by chromatography (silica, 0 to 100% ethyl acetate in heptane) afforded the title compound (3.75 g, 91%) as a white solid. MS: m/e=188.0 [M]+.

Aufarbeitung

  1. temperatureto warm up to room temperature over 1 h
  2. extractionextracted with ethyl acetate
  3. washthe combined organic extracts washed with brine
  4. dry with materialdried over sodium sulphate
  5. filtrationfiltered
  6. customevaporated
  7. customPurification by chromatography (silica, 0 to 100% ethyl acetate in heptane)

Quellen und Nachweise

ORD-Eintrag
ord-8f35a20d2cbe46eda1964ec8b8f0f3eb
Quelldatensatz
uspto-grants-2014_04
Patentnummer
US08697696B2

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