Aminoacetaldehyde dimethyl acetal → HCID 55103942, Verbindung

HRID 880504

Reaktionsgleichung

Reaktionsgleichung von HRID 880504
[CH3:1][O:2][CH:3]([O:6][CH3:7])[CH2:4][NH2:5].C(=O)(O)[O-].[Na+].[F:13][C:14]1[CH:15]=[C:16]([CH:20]=[CH:21][C:22]=1[N+:23]([O-:25])=[O:24])[C:17](Cl)=[O:18]>O1CCCC1>[CH3:1][O:2][CH:3]([O:6][CH3:7])[CH2:4][NH:5][C:17](=[O:18])[C:16]1[CH:20]=[CH:21][C:22]([N+:23]([O-:25])=[O:24])=[C:14]([F:13])[CH:15]=1

Komponenten

5

Edukt 3

HCID 89728Aminoacetaldehyde dimethyl acetalHCID 516892Sodium BicarbonateHCID 27746563-Fluoro-4-nitrobenzoyl chloride

Produkt 1

HCID 55103942HCID 55103942, VerbindungAusbeute 90 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

To a cooled solution of amino acetaldehyde dimethyl acetal (0.91 mL, 8.30 mmol) in dry tetrahydrofuran (15 mL) was added sodium bicarbonate (769 mg, 9.16 mmol) and then a solution of 3-fluoro-4-nitro-benzoyl chloride (1.7 g, 8.30 mmol) in dry tetrahydrofuran (15 mL) was added dropwise at 0° C. over a period of 30 min. The reaction mixture was stirred overnight at ambient temperature, the solvent was removed in vacuo, and the residue was diluted with water and extracted with ethyl acetate. The organic layer was washed with water, brine, dried over anhydrous sodium sulfate and concentrated to yield N-(2,2-dimethoxyethyl)-3-fluoro-4-nitro-benzamide (2.0 g, 90%) as a brown liquid.

Aufarbeitung

  1. customthe solvent was removed in vacuo
  2. additionthe residue was diluted with water
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with water, brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-04c7b18cf44d467fb5570f91c6069339
Quelldatensatz
uspto-grants-2015_03
Patentnummer
US08993574B2

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