Benzocaine → 4-(6-Bromo-4-methyl-3-oxo-3,4-dihydro-pyrazin-2-ylamino)-benzoic acid ethyl ester

HRID 551851

Reaktionsgleichung

Reaktionsgleichung von HRID 551851
Br[C:2]1[C:3](=[O:10])[N:4]([CH3:9])[CH:5]=[C:6]([Br:8])[N:7]=1.[NH2:11][C:12]1[CH:22]=[CH:21][C:15]([C:16]([O:18][CH2:19][CH3:20])=[O:17])=[CH:14][CH:13]=1.CN1CCCC1=O.[OH-].[Na+]>ClCCl>[CH2:19]([O:18][C:16](=[O:17])[C:15]1[CH:21]=[CH:22][C:12]([NH:11][C:2]2[C:3](=[O:10])[N:4]([CH3:9])[CH:5]=[C:6]([Br:8])[N:7]=2)=[CH:13][CH:14]=1)[CH3:20]

Komponenten

6

Edukt 4

HCID 2337BenzocaineHCID 13387N-methyl-2-pyrrolidoneHCID 14798Sodium HydroxideHCID 130629693,5-Dibromo-1-methyl-1H-pyrazin-2-one

Produkt 1

HCID 587289924-(6-Bromo-4-methyl-3-oxo-3,4-dihydro-pyrazin-2-ylamino)-benzoic acid ethyl esterAusbeute 76,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A mixture of 3,5-dibromo-1-methyl-2(1H)pyrazinone (1) (21.3 g; 79.5 mmol), ethyl 4-aminobenzoate (13.1 g; 79.5 mmol), and 1-methyl-2-pyrollidinone (10 mL) was heated at 130 degrees for 1 hr. The mixture was cooled to room temperature, diluted with dichloromethane and filtered to give a dull brown solid. This was slurried with 0.5N NaOH, filtered, washed with water and diethyl ether to give 4-(6-bromo-4-methyl-3-oxo-3,4-dihydro-pyrazin-2-ylamino)-benzoic acid ethyl ester (2) as a light brown solid (21.3 g)

Aufarbeitung

  1. temperaturewas heated at 130 degrees for 1 hr
  2. filtrationfiltered
  3. customto give a dull brown solid
  4. filtrationfiltered
  5. washwashed with water and diethyl ether

Quellen und Nachweise

ORD-Eintrag
ord-00cea9e78f9c4487b752bac8738a5b4d
Quelldatensatz
uspto-grants-2011_05
Patentnummer
US07947835B2

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