Cyclohexanethiol → HCID 59826863, Verbindung

HRID 239033

Reaktionsgleichung

Reaktionsgleichung von HRID 239033
[H-].[Na+].[CH:3]1([SH:9])[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4]1.Cl[C:11]1[N:18]=[C:17]([C:19]([F:22])([F:21])[F:20])[CH:16]=[CH:15][C:12]=1[C:13]#[N:14].[NH4+].[Cl-]>CN(C=O)C.O>[CH:3]1([S:9][C:11]2[N:18]=[C:17]([C:19]([F:22])([F:20])[F:21])[CH:16]=[CH:15][C:12]=2[C:13]#[N:14])[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4]1

Komponenten

7

Edukt 4

HCID 15290CyclohexanethiolHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 27784132-Chloro-6-(trifluoromethyl)nicotinonitrile

Produkt 1

HCID 59826863HCID 59826863, VerbindungAusbeute 94,6 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel2×

Versuchsvorschrift

1.3 Equivalents of NaH (4.9 g, 0.124 mol) were dissolved in 50 mL of DMF under a blanket of nitrogen. Following the addition of 1.2 equivalents of cyclohexanethiol (14.2 mL, 0.116 mol), the mixture was stirred at RT over a period of 1.5 h. The resulting suspension was cooled to 10° C. and added dropwise to 1 equivalent of 2-chloro-6-(trifluoromethyl)nicotinonitrile (20 g, 0.096 mol) in 50 mL of DMF and stirred over a period of 2 h at RT. To the reaction mixture there was added sat. aq. NH4Cl soln. and the mixture was diluted with 1 L of water and extracted with EA (3×200 mL). The combined organic phases were washed with sat. aq. NaCl solution, dried over MgSO4 and concentrated in vacuo. Column chromatographic purification (silica gel 100-200 mesh, eluant: 2% EA in hexane) yielded 26 g (93.8%) of product.

Aufarbeitung

  1. temperatureThe resulting suspension was cooled to 10° C.
  2. stirringstirred over a period of 2 h at RT
  3. extractionextracted with EA (3×200 mL)
  4. washThe combined organic phases were washed with sat. aq. NaCl solution
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated in vacuo
  7. customColumn chromatographic purification (silica gel 100-200 mesh, eluant: 2% EA in hexane)

Quellen und Nachweise

ORD-Eintrag
ord-5b3a03f7e2f541cd9acbddc0aaec5a1b
Quelldatensatz
uspto-grants-2014_02
Patentnummer
US08642775B2

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