Dimethyl Sulfoxide → HCID 57785864, Verbindung

HRID 1628707Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1628707
[Cl:1][C:2]1[C:10]2[N:9]=[C:8]3[N:11]([C:15]4[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][C:16]=4[C:22]([F:25])([F:24])[F:23])[CH2:12][CH2:13][CH2:14][N:7]3[C:6]=2[C:5]([CH2:26][OH:27])=[CH:4][CH:3]=1.C(N(CC)CC)C.CS(C)=O>ClCCl.C(=O)([O-])O.[Na+]>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH:26]=[O:27])=[C:6]2[C:10]=1[N:9]=[C:8]1[N:11]([C:15]3[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][C:16]=3[C:22]([F:24])([F:23])[F:25])[CH2:12][CH2:13][CH2:14][N:7]21

Komponenten

6

Edukt 3

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 57785948HCID 57785948, Verbindung

Produkt 1

HCID 57785864HCID 57785864, VerbindungAusbeute 80 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344DichloromethaneLösungsmittelHCID 516892Sodium BicarbonateLösungsmittel

Versuchsvorschrift

Sulfur trioxide-pyridine complex (23.4 g, 147 mmol) was added to a stirred solution of {9-chloro-1-[4-chloro-2-(trifluoromethyl)phenyl]-1,2,3,4-tetrahydropyrimido[1,2-a]benzimidazol-6-yl}methanol (8.72 g, 20.9 mmol), triethylamine (23.3 mL), and dimethyl sulfoxide (140 mL) in dichloromethane (30 mL) at room temperature, and the mixture was stirred at room temperature for 3 hr. The mixture was diluted with saturated aqueous sodium hydrogen carbonate, and extracted with ethyl acetate. The combined organic layer was washed with brine, dried over anhydrous magnesium sulfate, filtered and concentrated in vacuo. The residue was washed with diisopropyl ether to give the title compound as a colorless powder (6.90 g, 16.7 mmol, 80%).

Aufarbeitung

  1. extractionextracted with ethyl acetate
  2. washThe combined organic layer was washed with brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. washThe residue was washed with diisopropyl ether

Quellen und Nachweise

ORD-Eintrag
ord-c325b497b77c4cc7bfea0ad89e553aa3
Quelldatensatz
uspto-grants-2014_07
Patentnummer
US08785460B2

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