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

HRID 1844526Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1844526
[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-dimethyl-hydroxylamine (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-6105aef7d0964fabbaaa128ff4db3e04
Quelldatensatz
uspto-grants-2015_02
Patentnummer
US08946434B2

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