Ethyl Bromide → HCID 178436371, Verbindung

HRID 964165

Reaktionsgleichung

Reaktionsgleichung von HRID 964165
[CH2:1]([C:3]1[CH:4]=[C:5]([N:9]([CH2:12][CH3:13])C#N)[CH:6]=[CH:7][CH:8]=1)[CH3:2].[CH2:14]([C:16]1[CH:17]=[C:18]([NH:22][C:23]#[N:24])[CH:19]=[CH:20][CH:21]=1)[CH3:15].[H-].[Na+].[CH2:27](Br)[CH3:28]>C1COCC1.O.CO>[C:18]1([NH:22][C:23]([N:9]([C:5]2[CH:6]=[CH:7][CH:8]=[C:3]([CH2:1][CH3:2])[CH:4]=2)[CH2:12][CH3:13])=[NH:24])[C:17]2[C:16](=[CH:14][CH:15]=[CH:27][CH:28]=2)[CH:21]=[CH:20][CH:19]=1

Komponenten

8

Edukt 4

HCID 6332Ethyl BromideHCID 24758Sodium hydrideHCID 10012043[(3-Ethylphenyl)amino]carbonitrileHCID 10442201N-(m-ethylphenyl)-N-ethylcyanamide

Produkt 1

HCID 178436371HCID 178436371, VerbindungAusbeute 88 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 887MethanolLösungsmittelHCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

N-(m-Ethylphenyl)-N-ethylcyanamide: A suspension of m-ethylphenylcyanamide (2.26 g, 15.45 mmol) and sodium hydride (820 mg, 34.2 mmol, pre-washed thrice with hexane) in anhydrous THF (20 ml) was heated at 80°-85° C. for 2.5 hours. After it was allowed to cool to room temperature ethyl bromide (4.66 g, 42.76 mmol) was added and continued stirring at room temperature for 6 hours. Methanol (20 ml) followed by water (40 ml) were added and then extracted with dichloromethane (3×25 ml). Concentration of the organic layer followed by quick flash chromatography afforded the title compound (2.36 mg, 88%) as a light yellow liquid:

Aufarbeitung

  1. temperaturewas heated at 80°-85° C. for 2.5 hours
  2. additionwas added
  3. additionwere added
  4. extractionextracted with dichloromethane (3×25 ml)

Quellen und Nachweise

ORD-Eintrag
ord-3ec3ad3d56a3403b9c70b3acc494d195
Quelldatensatz
uspto-grants-1998_06
Patentnummer
US05767162

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