Pyridine → 4-phenyl-1-(N-chloroacetyl-2-methylindoline-5-sulfonyl)-2-imidazolone

HRID 1584663Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1584663
[C:1]1([C:7]2[NH:8][C:9](=[O:25])[N:10]([S:12]([C:15]3[CH:16]=[C:17]4[C:21](=[CH:22][CH:23]=3)[NH:20][CH:19]([CH3:24])[CH2:18]4)(=[O:14])=[O:13])[CH:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.N1C=CC=CC=1.[Cl:32][CH2:33][C:34](Cl)=[O:35]>ClCCl>[C:1]1([C:7]2[NH:8][C:9](=[O:25])[N:10]([S:12]([C:15]3[CH:16]=[C:17]4[C:21](=[CH:22][CH:23]=3)[N:20]([C:34](=[O:35])[CH2:33][Cl:32])[CH:19]([CH3:24])[CH2:18]4)(=[O:14])=[O:13])[CH:11]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Komponenten

5

Edukt 3

HCID 1049PyridineHCID 6577Chloroacetyl chlorideHCID 21224941HCID 21224941, Verbindung

Produkt 1

HCID 212248724-phenyl-1-(N-chloroacetyl-2-methylindoline-5-sulfonyl)-2-imidazoloneAusbeute 94 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

4-Phenyl-1-(2-methylindoline-5-sulfonyl)-2-imidazolone (300 mg, 0.85 mmol) prepared in Preparation 3 was dissolved in 10 ml of dichloromethane. Pyridine (75 μl, 0.93 mmol) and chloroacetylchloride (74 μl, 0.93 mmol) were added thereto one after another, and then the reaction mixture was stirred at room temperature under nitrogen atmosphere for 2 hours. After stirring, the reaction mixture was diluted with 50 ml of dichloromethane, washed with water, dried over anhydrous magnesium sulfate, and then concentrated. The residue was purified by silica gel column chromatography (eluent:dichloromethane/methanol=10/1, v/v) to afford 342 mg of the title compound as a white solid.

Aufarbeitung

  1. stirringAfter stirring
  2. washwashed with water
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated
  5. customThe residue was purified by silica gel column chromatography (eluent

Quellen und Nachweise

ORD-Eintrag
ord-34871b3043a84726b77fdeccfd9a307e
Quelldatensatz
uspto-grants-1999_08
Patentnummer
US05932742

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