Acetic Acid → 3-(Dimethylaminomethyl)-2-(methoxycarbonylamino)-6-(phenylthio) imidazo [1,2-a] pyridine

HRID 1413431Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1413431
[CH3:1][O:2][C:3]([NH:5][C:6]1[N:7]=[C:8]2[CH:13]=[CH:12][C:11]([S:14][C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)=[CH:10][N:9]2[CH:21]=1)=[O:4].[CH3:22][NH:23][CH3:24].C=O.[C:27](O)(=O)C>C(=O)(O)[O-].[Na+]>[CH3:22][N:23]([CH2:27][C:21]1[N:9]2[CH:10]=[C:11]([S:14][C:15]3[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=3)[CH:12]=[CH:13][C:8]2=[N:7][C:6]=1[NH:5][C:3]([O:2][CH3:1])=[O:4])[CH3:24]

Komponenten

6

Edukt 4

HCID 176Acetic AcidHCID 674DimethylamineHCID 712FormaldehydeHCID 12414300Methyl [6-(phenylsulfanyl)imidazo[1,2-a]pyridin-2-yl]carbamate

Produkt 1

HCID 545555143-(Dimethylaminomethyl)-2-(methoxycarbonylamino)-6-(phenylthio) imidazo [1,2-a] pyridine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 516892Sodium BicarbonateLösungsmittel

Versuchsvorschrift

2-(Methoxycarbonylamino)-6-(phenylthio) imidazo [1,2-a] pyridine (0.75 gm.) is added to a solution of 50% aqueous dimethylamine (0.215 gm., 37% formaldehyde (0.19 gm.) and acetic acid (0.35 g.) and heated at 50° C. for 3 hours. After cooling, the reaction mixture is diluted with aqueous sodium bicarbonate and the resultant precipitate is collected by filtration. After drying, the crude product is recrystallized from ethyl acetate to yield 3-(dimethylaminomethyl)-2-(methoxycarbonylamino)-6-(phenylthio) imidazo [1,2-a] pyridine m.p. 172°-175° C.

Aufarbeitung

  1. temperatureAfter cooling
  2. filtrationthe resultant precipitate is collected by filtration
  3. customAfter drying
  4. customthe crude product is recrystallized from ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-05dabc1b73884d4f8fca533e33e4d804
Quelldatensatz
uspto-grants-1981_02
Patentnummer
US04250174

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