Lithium hydroxide, monohydrate → N-[6-(3-aminophenoxy)-7-cyano-1,3-benzothiazol-2-yl]acetamide

HRID 455179

Reaktionsgleichung

Reaktionsgleichung von HRID 455179
[C:1]([NH:4][C:5]1[S:6][C:7]2[C:13]([C:14]#[N:15])=[C:12]([O:16][C:17]3[CH:18]=[C:19]([NH:23]C(=O)C(F)(F)F)[CH:20]=[CH:21][CH:22]=3)[CH:11]=[CH:10][C:8]=2[N:9]=1)(=[O:3])[CH3:2].O.[OH-].[Li+]>O1CCCC1.CO.O.C(OCC)(=O)C>[NH2:23][C:19]1[CH:18]=[C:17]([CH:22]=[CH:21][CH:20]=1)[O:16][C:12]1[CH:11]=[CH:10][C:8]2[N:9]=[C:5]([NH:4][C:1](=[O:3])[CH3:2])[S:6][C:7]=2[C:13]=1[C:14]#[N:15]

Komponenten

7

Edukt 2

HCID 168937Lithium hydroxide, monohydrateHCID 86644687N-(3-{[2-(Acetylamino)-7-cyano-1,3-benzothiazol-6-yl]oxy}phenyl)-2,2,2-trifluoroacetamide

Produkt 1

HCID 86644686N-[6-(3-aminophenoxy)-7-cyano-1,3-benzothiazol-2-yl]acetamideAusbeute 38,1 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 887MethanolLösungsmittelHCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel2×HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

N-(3-{[2-(Acetylamino)-7-cyano-1,3-benzothiazol-6-yl]oxy}phenyl)-2,2,2-trifluoroacetamide (6.8 g, 16.2 mmol) was dissolved in a mixed solvent of tetrahydrofuran (75 mL)/methanol (25 mL)/water (25 mL), lithium hydroxide monohydrate (1.99 g, 48.5 mmol) was added, and the mixture was stirred at room temperature for 20 hr. The reaction mixture was diluted with ethyl acetate (600 mL) and tetrahydrofuran (200 mL), washed successively with 5% aqueous sodium hydrogen carbonate solution (300 mL) and saturated brine (300 mL), and dried over anhydrous sodium sulfate. Insoluble material was filtered off, and the filtrate was concentrated under reduced pressure. The obtained residue was suspended in N,N-dimethylformamide/ethyl acetate (1:1), and the insoluble material was collected by filtration to give the title compound (2.00 g, 38%) as a white powder.

Aufarbeitung

  1. additionwas added
  2. washwashed successively with 5% aqueous sodium hydrogen carbonate solution (300 mL) and saturated brine (300 mL)
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationInsoluble material was filtered off
  5. concentrationthe filtrate was concentrated under reduced pressure
  6. filtrationthe insoluble material was collected by filtration

Quellen und Nachweise

ORD-Eintrag
ord-0bdc90c51b1e440aa85823e68eb7cc67
Quelldatensatz
uspto-grants-2013_07
Patentnummer
US08497274B2

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