Ammonia → 2-(Methoxycarbonylamino)-5-(phenylsulfinyl) imidazo [1,2-a] pyridine

HRID 372741Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 372741
Cl[C:2]1[CH:7]=[CH:6][C:5]([S:8]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[O:9])=CN=1.CN(C)P([N:23]([CH3:25])[CH3:24])(N(C)C)=O.[CH3:27][O:28][C:29](=[O:35])[NH:30][C:31](=O)CCl.[NH3:36]>CCOCC.CO>[CH3:27][O:28][C:29]([NH:30][C:31]1[N:36]=[C:25]2[CH:2]=[CH:7][CH:6]=[C:5]([S:8]([C:10]3[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=3)=[O:9])[N:23]2[CH:24]=1)=[O:35]

Komponenten

7

Edukt 4

HCID 222AmmoniaHCID 12679HexamethylphosphoramideHCID 518783methyl N-(2-chloroacetyl)carbamateHCID 203265612-Chloro-5-(phenylsulfinyl)pyridine

Produkt 1

HCID 536336252-(Methoxycarbonylamino)-5-(phenylsulfinyl) imidazo [1,2-a] pyridine

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 3283Diethyl EtherLösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

A solution of 2-chloro-5-(phenylsulfinyl)pyridine (2.37 g., .01 mole) in 10 ml. of hexamethylphosphoramide is treated with 2.2 g. of methylchloroacetylcarbamate. The solution is warmed to 50° C for 1 hour, cooled, combined with 5 ml. of methanol and saturated with anhydrous ammonia. The mixture is warmed at 100° C for 3 hours. After cooling, the reaction mixture is diluted with 5 volumes of ether and the crude product is collected by filtration. Recrystallization from hot methanol yields 2-(methoxycarbonylamino)-5-(phenylsulfinyl) imidazo [1,2-a] pyridine, m.p. 249°-251° C.

Aufarbeitung

  1. temperaturecooled
  2. temperatureThe mixture is warmed at 100° C for 3 hours
  3. temperatureAfter cooling
  4. filtrationthe crude product is collected by filtration
  5. customRecrystallization from hot methanol

Quellen und Nachweise

ORD-Eintrag
ord-db7c1e1e7d624561a632855206c1aa05
Quelldatensatz
uspto-grants-1978_05
Patentnummer
US04092321

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