3-(Dimethylamino)-2-propenal → HCID 178500406, Verbindung

HRID 1525640

Reaktionsgleichung

Reaktionsgleichung von HRID 1525640
[F:1][B-:2]([F:5])([F:4])[F:3].[NH+:6]1[CH:11]=[CH:10][CH:9]=C[CH:7]=1.[CH3:12][N:13]([CH3:18])[CH:14]=[CH:15][CH:16]=[O:17].[C:19](OC(=O)C)(=[O:21])C.[C:26](O)(=O)C>>[F:1][B-:2]([F:5])([F:4])[F:3].[CH3:12][N:13]([CH3:18])[CH:14]=[C:15]([C:16]([O:21][CH3:19])=[O:17])[CH:9]=[CH:10][CH:11]=[N+:6]([CH3:26])[CH3:7]

Komponenten

4

Edukt 3

HCID 791253-(Dimethylamino)-2-propenalHCID 11019233Borate(1-), tetrafluoro-, hydrogen, compd. with pyridine (1:1:1)HCID 21895370AcOH AcOAc

Produkt 1

HCID 178500406HCID 178500406, VerbindungAusbeute 65 %

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

Pyridiniumtetrafluoroborate (283.7 g, 1.70 mol) was added to a solution of methyl-(2E)-3-(3-dimethylamino)prop-2-enoate in 442.5 ml acetic anhydride/acetic acid (2:1). The resulting suspension was cooled to 0° C. and 3-dimethylaminoacroleine (169.9 ml, 1.70 mol) was added slowly (3 h) while vigorously stirring and cooling with an ice bath to yield a yellow-brown precipitate. After further stirring for 2 h at room temperature the reaction mixture was filtered. The remaining solid was washed with diethylether several times and dried under reduced pressure. Recrystallization from i-propanol/ethanol (2:1) gave 326.7 g (65%) of the pentamethinium salt as yellow crystals.

Aufarbeitung

  1. temperaturecooling with an ice bath
  2. customto yield a yellow-brown precipitate
  3. stirringAfter further stirring for 2 h at room temperature the reaction mixture
  4. filtrationwas filtered
  5. washThe remaining solid was washed with diethylether several times
  6. customdried under reduced pressure
  7. customRecrystallization from i-propanol/ethanol (2:1)

Quellen und Nachweise

ORD-Eintrag
ord-23874b87068d4fd291467d8c3ab55dfd
Quelldatensatz
uspto-grants-2015_07
Patentnummer
US09085535B2

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