Cyclohexane → 5-bromo-N,N-dimethyl-3-(trifluoromethyl)-1H-pyrazole-1-sulfonamide

HRID 1528543Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1528543
[CH3:1][N:2]([CH3:15])[S:3]([N:6]1[CH:10]=[CH:9][C:8]([C:11]([F:14])([F:13])[F:12])=[N:7]1)(=[O:5])=[O:4].C([Li])CCC.C1CCCCC1.[Br:27]Br>O1CCCC1>[Br:27][C:10]1[N:6]([S:3]([N:2]([CH3:15])[CH3:1])(=[O:5])=[O:4])[N:7]=[C:8]([C:11]([F:14])([F:12])[F:13])[CH:9]=1

Komponenten

6

Edukt 4

HCID 8078CyclohexaneHCID 24408BromineHCID 66826467N,N-dimethyl-3-(trifluoromethyl)-1H-pyrazole-1-sulfonamide2×HCID 178418339Butyllithium

Produkt 1

HCID 687456085-bromo-N,N-dimethyl-3-(trifluoromethyl)-1H-pyrazole-1-sulfonamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A stirred solution of N,N-dimethyl-3-(trifluoromethyl)-1H-pyrazole-1-sulfonamide (i.e. the product of Example 10, Step A) (4.25 g, 17.5 mmol) in tetrahydrofuran (50 mL) was cooled to −78° C., and then 2 M n-butyllithium in cyclohexane (10.0 mL, 20.0 mmol) was added dropwise. The reaction mixture was stirred a further 30 minutes, and then bromine (1.0 mL, 3.1 g, 18.7 mmol) was added dropwise. The reaction mixture was stirred for 10 minutes, warmed to room temperature, and quenched with brine (50 mL). The resulting solution was extracted with diethyl ether, dried (MgSO4), and concentrated under reduced pressure to give 6.77 g of title compound as a light yellow oil. This compound was of sufficient purity to use in subsequent reactions.

Aufarbeitung

  1. stirringThe reaction mixture was stirred for 10 minutes
  2. customquenched with brine (50 mL)
  3. extractionThe resulting solution was extracted with diethyl ether
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-e89dd55e7be44057838763833ee02cc1
Quelldatensatz
uspto-grants-2015_07
Patentnummer
US09090604B2

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