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Dimethylformamide → HCID 57736495, Verbindung

HRID 1641752
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1641752
Br[C:2]1[CH:7]=[C:6]([CH3:8])[C:5]([CH:9]([S:19][C:20]2[CH:21]=[N:22][C:23]([C:26]([F:29])([F:28])[F:27])=[CH:24][CH:25]=2)[C:10]2[C:15]([F:16])=[CH:14][CH:13]=[C:12]([F:17])[C:11]=2[F:18])=[CH:4][N:3]=1.C([Li])CCC.CN(C)[CH:37]=[O:38].[Cl-].[NH4+]>C1(C)C=CC=CC=1.O.ClCCl.CCCCCC>[CH3:8][C:6]1[C:5]([CH:9]([S:19][C:20]2[CH:21]=[N:22][C:23]([C:26]([F:27])([F:29])[F:28])=[CH:24][CH:25]=2)[C:10]2[C:15]([F:16])=[CH:14][CH:13]=[C:12]([F:17])[C:11]=2[F:18])=[CH:4][N:3]=[C:2]([CH:37]=[O:38])[CH:7]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

9

Edukt 4

HCID 6228DimethylformamideHCID 25517Ammonium ChlorideHCID 57736489HCID 57736489, VerbindungHCID 178418339Butyllithium

Produkt 1

HCID 57736495HCID 57736495, VerbindungAusbeute 59,1 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 962
Water
Lösungsmittel
HCID 1140TolueneLösungsmittel
HCID 6344DichloromethaneLösungsmittel
HCID 8058HexaneLösungsmittel

Reaktionsbedingungen

Temperatur
-40 °C

Versuchsvorschrift

To a solution of 2-bromo-4-methyl-5-[[[6-(trifluoromethyl)pyridin-3-yl]thio](2,3,6-trifluorophenyl)methyl]pyridine (4.76 g, 9.65 mmol) in toluene (100 ml), a hexane solution of n-butyllithium (1.58 M, 6.72 ml, 10.6 mmol) was added in an argon atmosphere at −78° C. The reaction mixture was stirred for 30 minutes at −40° C., and then cooled again to −78° C., and N,N-dimethylformamide (0.897 ml, 11.6 mmol) was added. After completion of dropwise addition, the reaction mixture was allowed to warm to 0° C., and saturated aqueous ammonium chloride was added thereto at the same temperature. Dichloromethane and water were added to the reaction mixture, and the organic layer was separated. Subsequently, the organic layer was dried over anhydrous sodium sulfate and filtered, and then the filtrate was concentrated under reduced pressure. The resulting residue was subjected to flash silica gel chromatography, and the fraction obtained from an elution with hexane:ethyl acetate=5:1 was concentrated under reduced pressure, to obtain the title compound (2.52 g, 5.70 mmol, 59%) as a yellow oily substance.

Aufarbeitung

  1. temperaturecooled again to −78° C.
  2. additionAfter completion of dropwise addition
  3. temperatureto warm to 0° C.
  4. customthe organic layer was separated
  5. dry with materialSubsequently, the organic layer was dried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. concentrationthe filtrate was concentrated under reduced pressure
  8. customthe fraction obtained from an elution with hexane
  9. concentrationethyl acetate=5:1 was concentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-68d839063b11489997f3206ddff0eeaa
Quelldatensatz
uspto-grants-2012_02
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08114886B2

Notizen zur Reaktion

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