N,O-Dimethylhydroxylamine → N-methoxy-N-methyl-2-(thiophen-3-yl)acetamide

HRID 924655Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 924655
[S:1]1[CH:5]=[CH:4][C:3]([CH2:6][C:7]([OH:9])=O)=[CH:2]1.[CH3:10][O:11][NH:12][CH3:13].CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1>C(Cl)Cl>[CH3:10][O:11][N:12]([CH3:13])[C:7](=[O:9])[CH2:6][C:3]1[CH:4]=[CH:5][S:1][CH:2]=1

Komponenten

6

Edukt 4

HCID 14232N,O-DimethylhydroxylamineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 234043-Thiophenacetic acidHCID 757711-Hydroxybenzotriazole

Produkt 1

HCID 11423995N-methoxy-N-methyl-2-(thiophen-3-yl)acetamideAusbeute 76,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

A mixture of 2-(thiophen-3-yl)acetic acid (2.0 g, 14.1 mmol), O,N-dimethylhydroxylamine (1.68 g, 16.9 mmol), EDCI (2.95 g, 15.5 mmol), HOBT (2.15 g, 15.5 mmol), and TEA (3.7 mL, 31 mmol) in anhydrous DCM (50 mL) was stirred at room temperature under nitrogen for two hours. The reaction mixture was diluted with CH2Cl2, and the organic layer was washed with aqueous HCl solution (0.5 mol/L, 30 mL×2), saturated NaHCO3 (30 mL×2) and brine(30 mL), dried over Na2SO4, filtered, and concentrated to give the crude N-methoxy-N-methyl-2-(thiophen-3-yl)acetamide (2.0 g, yield 76.6%).

Aufarbeitung

  1. washthe organic layer was washed with aqueous HCl solution (0.5 mol/L, 30 mL×2), saturated NaHCO3 (30 mL×2) and brine(30 mL)
  2. dry with materialdried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-03abfe3442b3403da377e9ce034b30ed
Quelldatensatz
uspto-grants-2016_03
Patentnummer
US09283213B2

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