Ethanol → 5-amino-6-fluoro-3-(5-methyl-1,2,4-oxadiazol-3-ylmethyl)-2(3H)-benzothiazolone

HRID 1199619Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1199619
[F:1][C:2]1[C:18]([N+:19]([O-])=O)=[CH:17][C:5]2[N:6]([CH2:10][C:11]3[N:15]=[C:14]([CH3:16])[O:13][N:12]=3)[C:7](=[O:9])[S:8][C:4]=2[CH:3]=1.C(O)C.[OH-].[K+]>Cl>[NH2:19][C:18]1[C:2]([F:1])=[CH:3][C:4]2[S:8][C:7](=[O:9])[N:6]([CH2:10][C:11]3[N:15]=[C:14]([CH3:16])[O:13][N:12]=3)[C:5]=2[CH:17]=1

Komponenten

5

Edukt 3

HCID 702EthanolHCID 14797Potassium HydroxideHCID 199794886-fluoro-3-(5-methyl-1,2,4-oxadiazol-3-ylmethyl)-5-nitro-2(3H)-benzothiazolone

Produkt 1

HCID 199794815-amino-6-fluoro-3-(5-methyl-1,2,4-oxadiazol-3-ylmethyl)-2(3H)-benzothiazoloneAusbeute 78,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 313Hydrochloric AcidLösungsmittel

Versuchsvorschrift

A mixture of 6-fluoro-3-(5-methyl-1,2,4-oxadiazol-3-yl-methyl)-5-nitro-2(3H)-benzothiazolone (3.1 g) and ethanol (40 ml) was prepared. To this mixture was dropwise added a solution of stannous chloride (3.3 mol equivalents per mol equivalent of the nitro compound) in concentrated hydrochloric acid (40 ml), at a temperature of 10° to 15° C. The reaction mixture was stirred at a temperature of 60° to 70° C. for 1.5 hours, and distilled under a reduced pressure to remove the ethanol and the hydrochloric acid therefrom. The resultant residue was admixed with ice (20 g). To the solution thus formed was added dropwise a 25% aqueous potassium hydroxide solution at a temperature of 10° to 15° C. to make the mixture alkaline. The mixture was extracted with dichloromethane (100 ml×2). The dichloromethane extract was washed with water, dried over anhydrous sodium sulfate, and evaporated under reduced pressure to obtain the aimed compound, i.e. 5-amino-6-fluoro-3-(5-methyl-1,2,4-oxadiazol-3-ylmethyl)-2(3H)-benzothiazolone (2.2 g). m.p. 158°-161° C.

Aufarbeitung

  1. customwas prepared
  2. customat a temperature of 10° to 15° C
  3. distillationdistilled under a reduced pressure
  4. customto remove the ethanol
  5. customTo the solution thus formed
  6. extractionThe mixture was extracted with dichloromethane (100 ml×2)
  7. extractionThe dichloromethane extract
  8. washwas washed with water
  9. dry with materialdried over anhydrous sodium sulfate
  10. customevaporated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-708b8856f7494907abe46bf1ae363e70
Quelldatensatz
uspto-grants-1990_02
Patentnummer
US04902335

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