1,2-Dichloroethane → 4-tert-Butyl-N-(2,2,8-trimethyl-4H-[1,3]dioxino[4,5-c]pyridin-5-yl-methyl)-benzamide

HRID 1158958

Reaktionsgleichung

Reaktionsgleichung von HRID 1158958
[CH3:1][C:2]1([CH3:15])[O:14][C:6]2=[C:7]([CH3:13])[N:8]=[CH:9][C:10]([CH2:11][NH2:12])=[C:5]2[CH2:4][O:3]1.[C:16]([C:20]1[CH:28]=[CH:27][C:23]([C:24](O)=[O:25])=[CH:22][CH:21]=1)([CH3:19])([CH3:18])[CH3:17].C(Cl)CCl.C(=O)(O)[O-].[Na+]>CN(C1C=CN=CC=1)C.ClCCl>[C:16]([C:20]1[CH:21]=[CH:22][C:23]([C:24]([NH:12][CH2:11][C:10]2[CH:9]=[N:8][C:7]([CH3:13])=[C:6]3[O:14][C:2]([CH3:15])([CH3:1])[O:3][CH2:4][C:5]=23)=[O:25])=[CH:27][CH:28]=1)([CH3:19])([CH3:17])[CH3:18]

Komponenten

7

Edukt 4

HCID 111,2-DichloroethaneHCID 74034-tert-Butylbenzoic acidHCID 516892Sodium BicarbonateHCID 12332441HCID 12332441, Verbindung

Produkt 1

HCID 586368334-tert-Butyl-N-(2,2,8-trimethyl-4H-[1,3]dioxino[4,5-c]pyridin-5-yl-methyl)-benzamideAusbeute 86,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A mixture of C-(2,2,8-trimethyl-4H-[1,3]dioxino[4,5-c]pyridin-5-yl)-methylamine (1.77 g, 8.49 mmol), 4-tert-butylbenzoic acid (5.6 g, 31 mmol), EDC (5.7 g, 29 mmol), and DMAP (4.53 g, 35.6 mmol) was stirred in dichloromethane (200 mL) for 24 hours. Saturated aqueous sodium bicarbonate was added to the reaction mixture, and the dichloromethane layer was separated. The aqueous layer was then extracted with dichloromethane. The combined organic layer was dried over anhydrous magnesium sulfate, filtered and evaporated. The crude mixture was purified by column chromatography on silica gel using a gradient mixture of dichloromethane:acetone (1:0 to 7:3) as eluant to give 4-tert-butyl-N-(2,2,8-trimethyl-4H-[1,3]dioxino[4,5-c]pyridin-5-yl-methyl)-benzamide (74) (2.7 g, 85%) as a light yellow solid.

Aufarbeitung

  1. customthe dichloromethane layer was separated
  2. extractionThe aqueous layer was then extracted with dichloromethane
  3. dry with materialThe combined organic layer was dried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. customevaporated
  6. customThe crude mixture was purified by column chromatography on silica gel using
  7. additiona gradient mixture of dichloromethane:acetone (1:0 to 7:3) as eluant

Quellen und Nachweise

ORD-Eintrag
ord-bf3ab3193be14c4da456ea2c04d3bfd6
Quelldatensatz
uspto-grants-2010_10
Patentnummer
US07812037B2

Verknüpfte Notizen

Wird geladen…