Cyclopropylamine → 3-(3-bromophenyl)-N-cyclopropylacrylamide
Reaktionsgleichung
[Br:1][C:2]1[CH:3]=[C:4]([CH:10]=[CH:11][CH:12]=1)/[CH:5]=[CH:6]/[C:7](Cl)=[O:8].[CH:13]1([NH2:16])[CH2:15][CH2:14]1>C1(C)C=CC=CC=1>[Br:1][C:2]1[CH:3]=[C:4]([CH:10]=[CH:11][CH:12]=1)/[CH:5]=[CH:6]/[C:7]([NH:16][CH:13]1[CH2:15][CH2:14]1)=[O:8]Komponenten
Edukt 2
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Versuchsvorschrift
A solution of trans 3-bromocinnamoyl chloride (12.2 g) in dry toluene (150 ml) was added dropwise (rapidly) with rapid stirring to a solution of cyclopropylamine (6.3 g) in dry toluene (150 ml). The reaction mixture was stirred at room temperature for 2 hours, then at 30°-35° C. for an additional hour; and the solvent and excess amine were removed under reduced pressure. The residue was triturated with water to remove cyclopropylamine hydrochloride. The product was filtered, washed with dilute hydrochloric acid and then with water. It was then recrystallized from ethanol:water (1:10) to give white crystalline trans 3-bromo-N-cyclopropylcinnamamide (12 g), m.p. 110°-111° C. Elemental analysis, NMR and 1R data were all consistent with the assigned structure. TLC gave one spot run on silica gel with 5:1 and with 3:1 hexane:ethanol.
Aufarbeitung
- waitat 30°-35° C. for an additional hour
- customand the solvent and excess amine were removed under reduced pressure
- customThe residue was triturated with water
- customto remove cyclopropylamine hydrochloride
- filtrationThe product was filtered
- washwashed with dilute hydrochloric acid
- customIt was then recrystallized from ethanol:water (1:10)
Quellen und Nachweise
- ORD-Eintrag
- ord-e149e2f0c44b4b1eb9cb638015eb0fed
- Quelldatensatz
- uspto-grants-1980_02
- Patentnummer
- US04190674
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