Methanesulfonyl chloride → HCID 57785826, Verbindung

HRID 1398970Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1398970
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]2[N:13]([CH2:14][CH2:15]O)[C:12]3[C:17]([CH:22]([CH2:25][CH3:26])[CH2:23][CH3:24])=[CH:18][CH:19]=[C:20]([Cl:21])[C:11]=3[N:10]=2)=[C:4]([Cl:27])[CH:3]=1.CS(Cl)(=O)=O>N1C=CC=CC=1>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:9]3=[N:10][C:11]4[C:20]([Cl:21])=[CH:19][CH:18]=[C:17]([CH:22]([CH2:25][CH3:26])[CH2:23][CH3:24])[C:12]=4[N:13]3[CH2:14][CH2:15]2)=[C:4]([Cl:27])[CH:3]=1

Komponenten

4

Edukt 2

HCID 31297Methanesulfonyl chlorideHCID 68767091HCID 68767091, Verbindung

Produkt 1

HCID 57785826HCID 57785826, VerbindungAusbeute 85 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1049PyridineLösungsmittel

Versuchsvorschrift

To a solution of 2-[2-[(4-bromo-2-chlorophenyl)amino]-4-chloro-7-(1-ethylpropyl)-1H-benzimidazol-1-yl]ethanol (Reference Example 23; 1.19 g, 2.53 mmol) in pyridine (6.0 mL) was added methanesulfonyl chloride (979 μL, 12.65 mmol) at 0° C. The reaction mixture was stirred at room temperature for 1.5 hr. The reaction mixture was quenched with saturated aqueous sodium hydrogen carbonate at 0° C. and extracted with ethyl acetate (×3). The combined organic layer was washed with brine, dried over anhydrous magnesium sulfate, filtered and concentrated in vacuo. The residue was purified by silica gel column chromatography eluting with a 0-15% ethyl acetate/n-hexane gradient mixture to give a solid. The resulting solid was recrystallized from n-hexane to give the title compound as a colorless powder (975.2 mg, 2.15 mmol, 85%).

Aufarbeitung

  1. customThe reaction mixture was quenched with saturated aqueous sodium hydrogen carbonate at 0° C.
  2. extractionextracted with ethyl acetate (×3)
  3. washThe combined organic layer was washed with brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by silica gel column chromatography
  8. washeluting with a 0-15% ethyl acetate/n-hexane gradient mixture
  9. customto give a solid
  10. customThe resulting solid was recrystallized from n-hexane

Quellen und Nachweise

ORD-Eintrag
ord-f9c7a92f9c0d495babe1e1d3563ef8c4
Quelldatensatz
uspto-grants-2014_12
Patentnummer
US08901141B2

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