Cyclohexanethiol → HCID 59826863, Verbindung

HRID 238253

Reaktionsgleichung

Reaktionsgleichung von HRID 238253
[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]>CN(C=O)C>[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

5

Edukt 3

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

Produkt 1

HCID 59826863HCID 59826863, VerbindungAusbeute 94,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel2×

Versuchsvorschrift

1.3 equivalents of NaH (4.9 g, 0.124 mol) were dissolved in 50 mL DMF under a nitrogen atmosphere. After the addition of 1.2 equivalents of cyclohexanethiol (14.2 mL, 0.116 mol), stirring was performed at room temperature for 1.5 h. The resultant suspension was cooled to 10° C. and 1 equivalent of 2-chloro-6-(trifluoromethyl)nicotinonitrile (20 g, 0.096 mol) in 50 mL DMF was added dropwise and stirred for 2 h at room temperature. The reaction mixture was quenched with sat. aq. NH4Cl soln., diluted with 1 l of water and extracted repeatedly with EA (3×200 mL). The combined organic phases were washed with a sat. aq. NaCl soln., dried over MgSO4 and evaporated under a vacuum. Purification performed by column chromatography (silica gel, 100-200 mesh, eluent: 2% EA in hexane) resulted in 26 g (93.8%) of product.

Aufarbeitung

  1. stirringstirred for 2 h at room temperature
  2. customThe reaction mixture was quenched with sat. aq. NH4Cl soln
  3. addition, diluted with 1 l of water
  4. extractionextracted repeatedly with EA (3×200 mL)
  5. washThe combined organic phases were washed with a sat. aq. NaCl soln
  6. dry with material, dried over MgSO4
  7. customevaporated under a vacuum
  8. customPurification

Quellen und Nachweise

ORD-Eintrag
ord-3550569e8347467a8b8f98f6a91718d3
Quelldatensatz
uspto-grants-2014_02
Patentnummer
US08642623B2

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