Hydrochloric Acid → HCID 59135994, Verbindung

HRID 2239123Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2239123
[OH:1][CH2:2][CH2:3][NH:4][CH2:5][CH2:6][CH:7]1[S:11][C:10]([C:12]2[NH:13][C:14]3[C:19]([CH:20]=2)=[CH:18][CH:17]=[CH:16][C:15]=3[N:21]([CH3:30])[S:22]([C:25]2[S:26][CH:27]=[CH:28][CH:29]=2)(=[O:24])=[O:23])=[N:9][CH2:8]1.Cl[CH2:32][C:33](Cl)=[O:34].[OH-].[Na+].Cl>C(O)C.O>[CH3:30][N:21]([C:15]1[CH:16]=[CH:17][CH:18]=[C:19]2[C:14]=1[NH:13][C:12]([C:10]1[S:11][CH:7]([CH2:6][CH2:5][N:4]3[CH2:3][CH2:2][O:1][CH2:32][C:33]3=[O:34])[CH2:8][N:9]=1)=[CH:20]2)[S:22]([C:25]1[S:26][CH:27]=[CH:28][CH:29]=1)(=[O:24])=[O:23]

Komponenten

7

Edukt 4

HCID 313Hydrochloric AcidHCID 6577Chloroacetyl chlorideHCID 14798Sodium HydroxideHCID 59136084N-[2-(5-{2-[(2-hydroxyethyl)amino]ethyl}-4,5-dihydro-1,3-thiazol-2-yl)-1H-indol-7-yl]-N-methylthiophene-2-sulfonamide

Produkt 1

HCID 59135994HCID 59135994, VerbindungAusbeute 41 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 702EthanolLösungsmittelHCID 962WaterLösungsmittel

Versuchsvorschrift

To a solution of N-[2-(5-{2-[(2-hydroxyethyl)amino]ethyl}-4,5-dihydro-1,3-thiazol-2-yl)-1H-indol-7-yl]-N-methylthiophene-2-sulfonamide (220 mg) in ethanol (2 mL) and water (1 mL) were added chloroacetyl chloride (95 μL) and 8M aqueous sodium hydroxide solution (310 μL), and the mixture was stirred at the inside temperature of 20° C. or less for 3 hr. 1M Hydrochloric acid was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with saturated aqueous sodium hydrogencarbonate and saturated brine, dried (MgSO4), and concentrated. The residue was subjected to silica gel column chromatography to give the title compound (100 mg, yield 41%) as a colorless amorphous solid from a fraction eluted with ethyl acetate-methanol (10:1, volume ratio).

Aufarbeitung

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe ethyl acetate layer was washed with saturated aqueous sodium hydrogencarbonate and saturated brine
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-bc463f9d93884599916510411d1f2f72
Quelldatensatz
uspto-grants-2010_05
Patentnummer
US07718798B2

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