1,3-Diethyl 2-oxopropanedioate → HCID 14152291, Verbindung

HRID 579834Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 579834
[Cl:1][C:2]1[CH:11]=[CH:10][C:5]2[NH:6][CH2:7][CH2:8][O:9][C:4]=2[CH:3]=1.[O:12]=[C:13]([C:19](OCC)=[O:20])[C:14]([O:16][CH2:17][CH3:18])=[O:15].C(=O)([O-])[O-].[NH4+].[NH4+]>C(O)(=O)C>[Cl:1][C:2]1[CH:3]=[C:4]2[O:9][CH2:8][CH2:7][N:6]3[C:19](=[O:20])[C:13]([OH:12])([C:14]([O:16][CH2:17][CH3:18])=[O:15])[C:10]([CH:11]=1)=[C:5]23

Komponenten

5

Edukt 3

HCID 691051,3-Diethyl 2-oxopropanedioateHCID 517111Ammonium CarbonateHCID 136432417-Chloro-3,4-dihydro-2H-1,4-benzoxazine

Produkt 1

HCID 14152291HCID 14152291, VerbindungAusbeute 77,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 176Acetic AcidLösungsmittel

Versuchsvorschrift

7-Chloro-3,4-dihydro-2H-1,4-benzoxazine (Japan Kokai JP No. 61-152984, U.S. Pat. No. 4,593,092) (19.77 g. 0.116 mol) was dissolved in 74 ml of acetic acid and to which diethyl ketomalonate 20.2 g (0.116 mol) was added dropwise at a room temperature. Then after refluxing for 20 minutes, the mixture was stand for overnight. After pouring into 500 ml of ice, ammonium carbonate was added to the solution. The resultant crystalline solid was collected by filtration, washed with water and dried to yield pale orange powders quantitatively. Recrystallization from ethanol afforded 26.67 g (77.3%) of the title compound as pale yellow prisms, mp 186°-187° C.

Aufarbeitung

  1. additionwas added dropwise at a room temperature
  2. temperatureThen after refluxing for 20 minutes
  3. customfor overnight
  4. additionwas added to the solution
  5. filtrationThe resultant crystalline solid was collected by filtration
  6. washwashed with water
  7. customdried
  8. customto yield pale orange powders quantitatively
  9. customRecrystallization from ethanol

Quellen und Nachweise

ORD-Eintrag
ord-91bfceae01904600b7777ac9cd0465cf
Quelldatensatz
uspto-grants-1988_06
Patentnummer
US04749789

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