Benzaldehyde → HCID 67773638, Verbindung

HRID 1963076Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1963076
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH2:8][CH2:9][N+:10]([O-:12])=[O:11])[C:3]=1[CH3:13].[CH:14](=O)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>C1(C)C=CC=CC=1.C(N)CCC.C(O)(=O)C>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH2:8][C:9]([N+:10]([O-:12])=[O:11])=[CH:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[C:3]=1[CH3:13]

Komponenten

6

Edukt 2

HCID 240Benzaldehyde2×HCID 677734531-Fluoro-2-methyl-3-(2-nitroethyl)benzene

Produkt 1

HCID 67773638HCID 67773638, VerbindungAusbeute 81,1 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 176Acetic AcidKatalysator2×HCID 8007ButylamineKatalysator2×HCID 1140TolueneLösungsmittel

Versuchsvorschrift

The compound of step 2 (17.951 g, 98 mmol), benzaldehyde (10.43 ml, 102.90 mmol), n-butylamine (0.49 ml, 4.90 mmol) and acetic acid (0.28 ml, 4.90 mmol) in 49 ml of toluene were heated at 180° C. in a Dean-Stark apparatus for 6 h. After cooling to room temperature, the mixture was evaporated to dryness under reduced pressure. The residue was taken up in 49 ml of toluene, benzaldehyde (10.43 ml, 102.90 mmol), n-butylamine (0.49 ml, 4.90 mmol) and acetic acid (0.28 ml, 4.90 mmol) were added, and the mixture was heated at 180° C. in a Dean-Stark apparatus for 3 h. After cooling to room temperature, the mixture was evaporated to dryness under reduced pressure. The residue was triturated with 25 ml of diethyl ether/pentane (1:1). The solid was filtered off, rinsed with cyclohexane, and dissolved in 75 ml of DCM. The solution was dried with magnesium sulfate and evaporated to dryness to give 21.57 g of the title compound as a yellow solid melting at 111-112° C.

Aufarbeitung

  1. customthe mixture was evaporated to dryness under reduced pressure
  2. temperaturethe mixture was heated at 180° C. in a Dean-Stark apparatus for 3 h
  3. temperatureAfter cooling to room temperature
  4. customthe mixture was evaporated to dryness under reduced pressure
  5. customThe residue was triturated with 25 ml of diethyl ether/pentane (1:1)
  6. filtrationThe solid was filtered off
  7. washrinsed with cyclohexane
  8. dissolutiondissolved in 75 ml of DCM
  9. dry with materialThe solution was dried with magnesium sulfate
  10. customevaporated to dryness

Quellen und Nachweise

ORD-Eintrag
ord-4a38a2672334485fb2cce25f11166507
Quelldatensatz
uspto-grants-2013_04
Patentnummer
US08415336B2

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