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1,3-Dibromopropane → Ethyl 6,7-dihydro-5H-pyrazolo(5,1-b)(1,3)oxazine-2-carboxylate

HRID 1158924
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1158924
[OH:1][C:2]1[NH:6][N:5]=[C:4]([C:7]([O:9][CH2:10][CH3:11])=[O:8])[CH:3]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:19][CH2:20][CH2:21]Br>C(#N)C>[N:5]1[N:6]2[C:2]([O:1][CH2:19][CH2:20][CH2:21]2)=[CH:3][C:4]=1[C:7]([O:9][CH2:10][CH3:11])=[O:8]
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Komponenten

5

Edukt 3

HCID 80011,3-DibromopropaneHCID 11430Potassium CarbonateHCID 178469373HCID 178469373, Verbindung

Produkt 1

HCID 11845247Ethyl 6,7-dihydro-5H-pyrazolo(5,1-b)(1,3)oxazine-2-carboxylateAusbeute 61,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

To the stirred suspension of ethyl 5-hydroxy-1H-pyrazole-3-carboxylate (10.34 g, 0.66 mol) and 36.62 g of potassium carbonate in 500 ml of acetonitrile was added 14.7 g of 1,3-dibromopropane, and refluxed for 16 hours. The reaction mixture was allowed to cool to room temperature, then filtered, the solid was washed with acetonitrile. The filtrate was concentrated to an oil. The residue was dissolved in ethyl acetate and extracted with water. The organic phase was dried over MgSO4 and evaporated to dryness. 8.80 g of the desired product was obtained (68%), m.p. 44-46° C. (M+H)+ 197.1.

Aufarbeitung

  1. temperaturerefluxed for 16 hours
  2. filtrationfiltered
  3. washthe solid was washed with acetonitrile
  4. concentrationThe filtrate was concentrated to an oil
  5. dissolutionThe residue was dissolved in ethyl acetate
  6. extractionextracted with water
  7. dry with materialThe organic phase was dried over MgSO4
  8. customevaporated to dryness

Quellen und Nachweise

ORD-Eintrag
ord-375ad53ea13e4f8d81c0f45da17b401f
Quelldatensatz
uspto-grants-2010_10
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07812014B2

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