4-Toluenesulfonyl chloride → HCID 24805800, Verbindung

HRID 522724Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 522724
[F:1][C:2]([F:9])([F:8])[C:3]1([CH2:6][OH:7])[CH2:5][CH2:4]1.[CH3:10][C:11]1[CH:16]=[CH:15][C:14]([S:17](Cl)(=[O:19])=[O:18])=[CH:13][CH:12]=1>C(Cl)Cl.CN(C)C1C=CN=CC=1>[CH3:10][C:11]1[CH:16]=[CH:15][C:14]([S:17]([O:7][CH2:6][C:3]2([C:2]([F:9])([F:8])[F:1])[CH2:5][CH2:4]2)(=[O:19])=[O:18])=[CH:13][CH:12]=1

Komponenten

5

Edukt 2

HCID 73974-Toluenesulfonyl chlorideHCID 509906611-(Trifluoromethyl)cyclopropanemethanol

Produkt 1

HCID 24805800HCID 24805800, VerbindungAusbeute 81,6 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

Treat a solution of (1-(trifluoromethyl)cyclopropyl)methanol (7 g, 50 mmol) and 4-methylbenzene-1-sulfonyl chloride (10.4 g, 55 mmol) in anhydrous DCM (100 mL) with TEA (10 g, 100 mmol) and N,N-dimethylpyridin-4-amine (0.6 g, 5 mmol). Stir at RT overnight. Wash the mixture successively with HCl (2M), saturated NaHCO3, and brine, dry over Na2SO4 and concentrate under reduced pressure to give the title compound (12 g, 81% yield). 1H NMR (400 MHz, DMSO-d6): δ 7.79 (d, J=8.0 Hz, 2H), 7.50 (d, J=8.0 Hz, 2H), 4.13 (s, 2H), 2.43 (s, 3H), 1.08-1.05 (m, 2H), 0.96-0.94 (m, 2H).

Aufarbeitung

  1. washWash the mixture successively with HCl (2M), saturated NaHCO3, and brine
  2. dry with materialdry over Na2SO4
  3. concentrationconcentrate under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-63256913ff1c41ef8d238a774484e5cc
Quelldatensatz
uspto-grants-2016_05
Patentnummer
US09334267B2

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