Sodium hydride → HCID 22638837, Verbindung

HRID 1836655

Reaktionsgleichung

Reaktionsgleichung von HRID 1836655
CCOP(OCC)([CH2:6][C:7]([N:9]([O:11][CH3:12])[CH3:10])=[O:8])=O.[H-].[Na+].[S:18]1[CH:22]=[C:21]([CH:23]=O)[C:20]2[CH:25]=[CH:26][CH:27]=[CH:28][C:19]1=2>C1COCC1>[S:18]1[CH:22]=[C:21](/[CH:23]=[CH:6]/[C:7]([N:9]([O:11][CH3:12])[CH3:10])=[O:8])[C:20]2[CH:25]=[CH:26][CH:27]=[CH:28][C:19]1=2

Komponenten

5

Edukt 3

HCID 24758Sodium hydrideHCID 2273281-Benzothiophene-3-carbaldehydeHCID 2773719Diethyl (N-methoxy-N-methylcarbamoylmethyl)phosphonate

Produkt 1

HCID 22638837HCID 22638837, VerbindungAusbeute 93,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

Diethyl (N-methoxy-N-methylcarbamoylmethyl)phosphonate (6.13 g, 25.6 mmol) was added dropwise via syringe to a stirred suspension of sodium hydride (1.02 g, 25.6 mmol) in anhydrous THF (75 ml) at 0° C. The reaction was warmed to room temperature and was stirred for 1 h. After cooling to 0° C., benzo[b]thiophene-3-carbaldehyde (3.78 g, 23.3 mmol) was added. The resulting mixture was stirred at room temperature for 1 hr. The reaction was quenched with 100 mL aqueous HCl (0.1 N) and extracted with ethyl acetate (250 ml). The combined organic layers were washed with brine (50 ml) and dried over anhydrous magnesium sulfate. The filtrate was concentrated in vacuo and triturated with hexane to give (E)-3-benzo[b]thiophen-3-yl-N-methoxy-N-methyl-acrylamide (5.38 g, 93%) as a yellow solid. 1H NMR (500 MHz, CDCl3) 8.06-8.01 (2H, 2 superimposed d, J=8.24, 15.87 Hz), 7.89 (1H, d, J=7.94 Hz), 7.78 (1H, s), 7.47 (1H, t, J=7.93 Hz), 7.41 (1H, t, J=8.24 Hz), 7.13 (1H, d, J=15.87 Hz), 3.79 (3H, s), 3.34 (3H, s); MS m/e 248.07 (M+H)+.

Aufarbeitung

  1. temperatureAfter cooling to 0° C.
  2. stirringThe resulting mixture was stirred at room temperature for 1 hr
  3. customThe reaction was quenched with 100 mL aqueous HCl (0.1 N)
  4. extractionextracted with ethyl acetate (250 ml)
  5. washThe combined organic layers were washed with brine (50 ml)
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationThe filtrate was concentrated in vacuo
  8. customtriturated with hexane

Quellen und Nachweise

ORD-Eintrag
ord-090caecb407a4a1b9194ab951b99cd35
Quelldatensatz
uspto-grants-2004_08
Patentnummer
US06777437B2

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