Sodium hydride → HCID 86759694, Verbindung

HRID 2179957Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2179957
[H-].[Na+].[OH:3][CH:4]([C:15]1[CH:16]=[N:17][CH:18]=[CH:19][CH:20]=1)[CH2:5][CH2:6][NH:7][C:8](=[O:14])[O:9][C:10]([CH3:13])([CH3:12])[CH3:11].[Cl:21][C:22]1[C:29]([F:30])=[CH:28][C:25]([C:26]#[N:27])=[C:24](F)[CH:23]=1>O1CCCC1>[Cl:21][C:22]1[C:29]([F:30])=[CH:28][C:25]([C:26]#[N:27])=[C:24]([CH:23]=1)[O:3][CH:4]([C:15]1[CH:16]=[N:17][CH:18]=[CH:19][CH:20]=1)[CH2:5][CH2:6][NH:7][C:8](=[O:14])[O:9][C:10]([CH3:13])([CH3:12])[CH3:11]

Komponenten

5

Edukt 3

HCID 24758Sodium hydrideHCID 112753024-Chloro-2,5-difluorobenzonitrileHCID 69799429[3-Hydroxy-3-(3-pyridinyl)propyl]carbamic acid 1,1-dimethylethyl ester

Produkt 1

HCID 86759694HCID 86759694, VerbindungAusbeute 88 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

Sodium hydride (141 mg, 60% dispersion in oil) was added to a solution of the product from step (b) (785 mg, 2.96 mmol) and 4-chloro-2,5-difluorobenzonitrile (546 mg, 3.75 mmol) in tetrahydrofuran (9 ml) and the resultant suspension was stirred for 0.5 h. The mixture was quenched with saturated aqueous ammonium chloride, basified to pH 8 and extracted with ethyl acetate (three times). The combined organic extracts were dried (sodium sulphate), evaporated and purified by chromatography on silica eluting with petrol—acetone to give 1.05 g (88%) of the sub-title compound as a colourless oil.

Aufarbeitung

  1. customThe mixture was quenched with saturated aqueous ammonium chloride
  2. extractionextracted with ethyl acetate (three times)
  3. dry with materialThe combined organic extracts were dried (sodium sulphate)
  4. customevaporated
  5. custompurified by chromatography on silica eluting with petrol—acetone

Quellen und Nachweise

ORD-Eintrag
ord-e90cccf4c60846e3b9d4703c2fbf62f6
Quelldatensatz
uspto-grants-2005_05
Patentnummer
US06887871B2

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