Hydrochloric Acid → 6-(2-chloroethyl)-7-methyl-5H-(1,3)thiazolo(3,2-a)pyrimidin-5-one

HRID 256645

Reaktionsgleichung

Reaktionsgleichung von HRID 256645
[S:1]1[CH:5]=[CH:4][N:3]=[C:2]1[NH2:6].[C:7]([CH:10]1[CH2:14][CH2:13][O:12][C:11]1=O)(=O)[CH3:8].Cl.P(Cl)(Cl)([Cl:19])=O>O.CC1C=CC=CC=1>[Cl:19][CH2:13][CH2:14][C:10]1[C:11](=[O:12])[N:3]2[CH:4]=[CH:5][S:1][C:2]2=[N:6][C:7]=1[CH3:8]

Komponenten

7

Edukt 4

HCID 313Hydrochloric AcidHCID 21552-AminothiazoleHCID 106012-AcetylbutyrolactoneHCID 24813Phosphorus oxychloride

Produkt 1

HCID 8178726-(2-chloroethyl)-7-methyl-5H-(1,3)thiazolo(3,2-a)pyrimidin-5-one

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 1140TolueneLösungsmittel

Versuchsvorschrift

A mixture of 50 parts of 2-thiazolamine, 76 parts of 3-acetyl-4,5-dihydro-2(3H)-furanone, 1.2 parts of concentrated hydrochloric acid and 270 parts of methylbenzene was stirred and refluxed for 2 hours using a water-separator. The reaction mixture was cooled and 340 parts of phosphoryl chloride were added at a temperature between 20° and 30° C. The whole was heated slowly to 100°~110° C. and stirring was continued for 2 hours at this temperature. The reaction mixture was evaporated and the residue was poured into a mixture of crushed ice and ammonium hydroxide. The product was extracted with trichloromethane. The extract was dried. filtered and evaporated. The residue was purified by column chromatography over silica gel using a mixture of trichloromethane and methanol (95:5 by volume) as eluent. The pure fractions were collected and the eluent was evaporated. The residue was crystallized from a mixture of 2-propanol and 1,1'-oxybisethane, yielding 36 parts of 6-(2 -chloroethyl)-7-methyl-5H-thiazolo[3,2-a]pyrimidin-5-one (interm. 48).

Aufarbeitung

  1. temperaturerefluxed for 2 hours
  2. temperatureThe reaction mixture was cooled
  3. temperatureThe whole was heated slowly to 100°~110° C.
  4. stirringstirring
  5. customThe reaction mixture was evaporated
  6. additionthe residue was poured into a mixture of crushed ice and ammonium hydroxide
  7. extractionThe product was extracted with trichloromethane
  8. customThe extract was dried
  9. filtrationfiltered
  10. customevaporated
  11. customThe residue was purified by column chromatography over silica gel using
  12. additiona mixture of trichloromethane and methanol (95:5 by volume) as eluent
  13. customThe pure fractions were collected
  14. customthe eluent was evaporated
  15. customThe residue was crystallized from a mixture of 2-propanol and 1,1'-oxybisethane

Quellen und Nachweise

ORD-Eintrag
ord-ffa1f463e2b94e5c8f0b90dbe81f1a4b
Quelldatensatz
uspto-grants-1993_11
Patentnummer
US05258380

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