Methanol → 3-(3-Benzothiazol-6-yl-2-oxo-imidazolidin-1-yl)-pyridine-4-carbaldehyde

HRID 2383923

Reaktionsgleichung

Reaktionsgleichung von HRID 2383923
CC1C=CC(S(O)(=O)=O)=CC=1.[S:12]1[C:16]2[CH:17]=[C:18]([N:21]3[CH2:25][CH2:24][N:23]([C:26]4[CH:27]=[N:28][CH:29]=[CH:30][C:31]=4[CH:32](OC)[O:33]C)[C:22]3=[O:37])[CH:19]=[CH:20][C:15]=2[N:14]=[CH:13]1.CO>CC(C)=O.O.C(Cl)(Cl)Cl>[S:12]1[C:16]2[CH:17]=[C:18]([N:21]3[CH2:25][CH2:24][N:23]([C:26]4[CH:27]=[N:28][CH:29]=[CH:30][C:31]=4[CH:32]=[O:33])[C:22]3=[O:37])[CH:19]=[CH:20][C:15]=2[N:14]=[CH:13]1

Komponenten

7

Edukt 3

HCID 887MethanolHCID 6101p-Toluenesulfonic acidHCID 498724521-Benzothiazol-6-yl-3-(4-dimethoxymethyl-pyridin-3-yl)-imidazolidin-2-one

Produkt 1

HCID 596362723-(3-Benzothiazol-6-yl-2-oxo-imidazolidin-1-yl)-pyridine-4-carbaldehydeAusbeute 99,5 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 180AcetoneLösungsmittelHCID 962WaterLösungsmittelHCID 6212ChloroformLösungsmittel

Versuchsvorschrift

PTSA (2.2 g, 11.672 mmol) was added to a stirred solution of 1-benzothiazol-6-yl-3-(4-dimethoxymethyl-pyridin-3-yl)-imidazolidin-2-one (I-177a: 460 mg, 1.2418 mmol) in acetone (20 mL) and water (20 mL). The resulting reaction mass was stirred for 48 hours at room temperature. The reaction was monitored by TLC (5% methanol in chloroform). The reaction mixture was concentrated, the residue was diluted with ice-water, basified with saturated NaHCO3 solution and extracted using ethyl acetate. The aqueous layer was filtered and the solid collected was dried under reduced pressure. The solid was dissolved in methanol and chloroform, dried over Na2SO4 and concentrated under reduced pressure to afford 400 mg of the product (99.5% yield).

Aufarbeitung

  1. customThe resulting reaction mass
  2. concentrationThe reaction mixture was concentrated
  3. additionthe residue was diluted with ice-water
  4. extractionextracted
  5. filtrationThe aqueous layer was filtered
  6. customthe solid collected
  7. customwas dried under reduced pressure
  8. dissolutionThe solid was dissolved in methanol
  9. dry with materialchloroform, dried over Na2SO4
  10. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-73b9021cf1714944acb1183ab0fcd82f
Quelldatensatz
uspto-grants-2012_09
Patentnummer
US08263635B2

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