Triethylamine → HCID 18334081, Verbindung

HRID 2269497Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2269497
[N+:1]([C:4]1[CH:5]=[C:6]([C:10]([C:12]2[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=2)=O)[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2].[C:20]([NH2:29])([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)([CH3:22])[CH3:21].C(N(CC)CC)C.C([BH3-])#N.[Na+]>ClCCl.C(OCC)(=O)C.[Ti](Cl)(Cl)(Cl)Cl.C(O)(=O)C.C(O)C>[CH3:19][O:18][C:15]1[CH:16]=[CH:17][C:12]([CH:10]([C:6]2[CH:7]=[CH:8][CH:9]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=2)[NH:29][C:20]([CH3:22])([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH3:21])=[CH:13][CH:14]=1

Komponenten

10

Edukt 4

HCID 8471TriethylamineHCID 68509CumylamineHCID 794540(4-Methoxyphenyl)(3-nitrophenyl)methanoneHCID 5003444Sodium cyanoborohydride

Produkt 1

HCID 18334081HCID 18334081, VerbindungAusbeute 38 %

Reagenzien, Katalysatoren, Lösungsmittel 5

HCID 24193Titanium TetrachlorideKatalysatorHCID 176Acetic AcidLösungsmittelHCID 702EthanolLösungsmittelHCID 6344DichloromethaneLösungsmittel2×HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

2.57 g of 4-methoxyphenyl 3-nitrophenyl ketone, 1.35 g of cumyl amine and 1.35 g of triethylamine were dissolved in 50 ml of dichloromethane, and then 30 ml of a solution of 1.65 ml of titanium tetrachloride in dichloromethane was added dropwise whilst ice cooling. The reaction mixture was stirred at room temperature for 2 hours and was then heated under reflux for 3 hours. The reaction mixture was allowed to cool, after which it was diluted with 150 ml of ethyl acetate. The insoluble matter was then filtered off. The filtrate was washed with a saturated solution of sodium hydrogencarbonate and with a saturated aqueous solution of sodium chloride, dried over anhydrous magnesium sulfate and distilled under reduced pressure to remove the solvent. Following a similar reaction, separation and purification procedure to that described in Example (1a), the resulting brown oil, 100 ml of ethanol 2.51 g of sodium cyanoborohydride and 2.58 ml of acetic acid were reacted, to obtain 1.43 g of the title compound as a yellow oil.

Aufarbeitung

  1. temperaturewas then heated
  2. temperatureunder reflux for 3 hours
  3. temperatureto cool
  4. filtrationThe insoluble matter was then filtered off
  5. washThe filtrate was washed with a saturated solution of sodium hydrogencarbonate and with a saturated aqueous solution of sodium chloride
  6. dry with materialdried over anhydrous magnesium sulfate
  7. distillationdistilled under reduced pressure
  8. customto remove the solvent
  9. customa similar reaction, separation and purification procedure to

Quellen und Nachweise

ORD-Eintrag
ord-fbc68857273849b89ee276d2977c81e1
Quelldatensatz
uspto-grants-2001_12
Patentnummer
US06329405B1

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