5H-Dibenzo(a,d)cycloheptene, 10,11-dihydro-5-chloro- → Ethyl alpha-[(diphenylmethylene)amino]-10,11,dihydro-5H-dibenzo[a,d]cycloheptene-5-acetate

HRID 258194

Reaktionsgleichung

Reaktionsgleichung von HRID 258194
[C:1]1([C:7]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[N:8][CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH2:21]1[C:35]2[C:30](=[CH:31][CH:32]=[CH:33][CH:34]=2)[CH:29](Cl)[C:28]2[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=2)[CH2:22]1.[OH-].[Na+]>ClCCl.[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.O.C(OCC)C>[C:1]1([C:7](=[N:8][CH:9]([CH:29]2[C:28]3[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=3[CH2:22][CH2:21][C:35]3[CH:34]=[CH:33][CH:32]=[CH:31][C:30]2=3)[C:10]([O:12][CH2:13][CH3:14])=[O:11])[C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Komponenten

8

Edukt 3

HCID 145875H-Dibenzo(a,d)cycloheptene, 10,11-dihydro-5-chloro-HCID 14798Sodium HydroxideHCID 319508Ethyl 2-(diphenylmethyleneamino)acetate

Produkt 1

HCID 19385932Ethyl alpha-[(diphenylmethylene)amino]-10,11,dihydro-5H-dibenzo[a,d]cycloheptene-5-acetateAusbeute 101,5 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 74236Tetrabutylammonium BromideKatalysatorHCID 962WaterLösungsmittel2×HCID 3283Diethyl EtherLösungsmittelHCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

Ethyl N-(diphenylmethylene)glycinate (12 g, 45 mmol) and 5-chlorodibenzosuberane (12.32 g, 54 mmol) are dissolved in 250 mL of dichloromethane, tetrabutylammonium bromide (17.6 g, 55 mmol) and 47 mL of 50% sodium hydroxide solution are added and the mixture is mechanically stirred at room temperature for 4 hours. Then it is diluted with 75 mL of dichloromethane and water and the layers are separated. The organic layer is washed with water, dried over magnesium sulfate, filtered, and stripped under vacuum to give a brown orange oil. The oil is taken up in 250 mL of diethyl ether and 100 mL of water. The diethyl ether solution is additionally washed with water, dried (magnesium sulfate), and stripped to give a clear red-orange sticky oil residue (~21 g) which is used in the next step without purification.

Aufarbeitung

  1. customthe layers are separated
  2. washThe organic layer is washed with water
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. customto give a brown orange oil
  6. washThe diethyl ether solution is additionally washed with water
  7. dry with materialdried (magnesium sulfate)

Quellen und Nachweise

ORD-Eintrag
ord-3d85d073429848d7a0bae10a9d71d26a
Quelldatensatz
uspto-grants-1993_11
Patentnummer
US05264577

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