Chloroacetaldehyde → 3-Hydroxy-6-(3-nitrophenyl)-7-pyridin-4-yl-2,3-dihydro-pyrazolo[5,1-b]thiazole

HRID 38091

Reaktionsgleichung

Reaktionsgleichung von HRID 38091
[N+:1]([C:4]1[CH:5]=[C:6]([C:10]2[C:11]([C:16]3[CH:21]=[CH:20][N:19]=[CH:18][CH:17]=3)=[C:12]([SH:15])[NH:13][N:14]=2)[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2].Cl[CH2:23][CH:24]=[O:25]>C1COCC1.O.CCOC(C)=O.C([O-])(O)=O.[Na+]>[OH:25][CH:24]1[CH2:23][S:15][C:12]2=[C:11]([C:16]3[CH:21]=[CH:20][N:19]=[CH:18][CH:17]=3)[C:10]([C:6]3[CH:7]=[CH:8][CH:9]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=3)=[N:14][N:13]12

Komponenten

6

Edukt 2

HCID 33ChloroacetaldehydeHCID 178526614HCID 178526614, Verbindung

Produkt 1

HCID 674426243-Hydroxy-6-(3-nitrophenyl)-7-pyridin-4-yl-2,3-dihydro-pyrazolo[5,1-b]thiazoleAusbeute 72,7 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 8857Ethyl AcetateLösungsmittelHCID 516892Sodium BicarbonateLösungsmittelHCID 21881883Oxolane--water (1/1)Lösungsmittel

Versuchsvorschrift

5-(3-Nitro-phenyl)-4-pyridin-4-yl-2H-pyrazole-3-thiol (prepared as described in Example 1) (3.92 g, 13.14 mmol) was dissolved in a 1:1 THF/water mixture (130 mL). Chloroacetaldehyde (55% in water, 2.31 mL, 19.71 mmol, 1.5 eq) was added and the solution was stirred at room temperature overnight. The reaction mixture was diluted with AcOEt and saturated aqueous NaHCO3. The organic phase was washed with saturated aqueous NaHCO3 and brine, dried and evaporated to dryness. 3.25 g of crude product were obtained as yellow solid (72%), which was used in the following step without further purification.

Aufarbeitung

  1. washThe organic phase was washed with saturated aqueous NaHCO3 and brine
  2. customdried
  3. customevaporated to dryness

Quellen und Nachweise

ORD-Eintrag
ord-077782a335c4497a9139fd5fd4e839e6
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08524707B2

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