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Hydroxylamine → 1-(2,2-Dimethoxyethyl)-1,6-dihydro-N-hydroxy-6-oxo-2-phenyl-5-pyrimidinecarboxamide

HRID 1862069
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1862069
C(N(CC)CC)C.[CH3:8][O:9][CH:10]([O:28][CH3:29])[CH2:11][N:12]1[C:17](=[O:18])[C:16]([C:19](O)=[O:20])=[CH:15][N:14]=[C:13]1[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.C(Cl)(=O)OCC(C)C.[NH2:38][OH:39]>O1CCCC1>[OH:39][NH:38][C:19]([C:16]1[C:17](=[O:18])[N:12]([CH2:11][CH:10]([O:28][CH3:29])[O:9][CH3:8])[C:13]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[N:14][CH:15]=1)=[O:20]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 787HydroxylamineHCID 8471TriethylamineHCID 62365Isobutyl chloroformateHCID 117225541-(2,2-Dimethoxyethyl)-6-oxo-2-phenyl-1,6-dihydropyrimidine-5-carboxylic acid

Produkt 1

HCID 97970941-(2,2-Dimethoxyethyl)-1,6-dihydro-N-hydroxy-6-oxo-2-phenyl-5-pyrimidinecarboxamideAusbeute 91 %

Reagenzien, Katalysatoren, Lösungsmittel

1
HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

Triethylamine (49.4 ml) was added to a solution of 1-(2,2-dimethoxyethyl)-6-oxo-2-phenyl-1,6-dihydropyrimidin-5-ylcarboxylic acid (97.3 g) in tetrahydrofuran (800 ml) in an ice bath in an argon atmosphere, and isobutyl chlorocarbonate (45.6 ml) was added dropwise thereto at 5° C. or lower, followed by stirring at the same temperature for 1 hour. To the reaction mixture was added a 50% hydroxylamine aqueous solution (422 ml), followed by stirring for 20 minutes. The reaction mixture was separated to layers. The aqueous layer was extracted with ethyl acetate (200 ml). The organic layers were combined, washed with saturated saline (200 ml), and concentrated. To the residue was added toluene (200 ml), followed by concentration. The resulting crude crystals were washed with isopropyl ether (1000 ml) by heating under reflux for 10 minutes, cooled to room temperature, and crystals were collected by filtration. The collected crystals were dried in vacuo at room temperature overnight to obtain the title compound (93.3 g; yield: 91%) having the following physical properties.

Aufarbeitung

  1. additionwas added dropwise
  2. customat 5° C.
  3. stirringby stirring for 20 minutes
  4. customThe reaction mixture was separated to layers
  5. extractionThe aqueous layer was extracted with ethyl acetate (200 ml)
  6. washwashed with saturated saline (200 ml)
  7. concentrationconcentrated
  8. additionTo the residue was added toluene (200 ml)
  9. concentrationfollowed by concentration
  10. washThe resulting crude crystals were washed with isopropyl ether (1000 ml)
  11. temperatureby heating
  12. temperatureunder reflux for 10 minutes
  13. filtrationcrystals were collected by filtration
  14. customThe collected crystals were dried in vacuo at room temperature overnight

Quellen und Nachweise

ORD-Eintrag
ord-c06fee7a81ca4632ab966d2e788c6a59
Quelldatensatz
uspto-grants-2003_03
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06534658B1

Notizen zur Reaktion

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