Nitrourea → Dezinamide

HRID 974582

Reaktionsgleichung

Reaktionsgleichung von HRID 974582
[F:1][C:2]([F:15])([F:14])[C:3]1[CH:4]=[C:5]([CH:11]=[CH:12][CH:13]=1)[O:6][CH:7]1[CH2:10][NH:9][CH2:8]1.[N+]([NH:19][C:20](N)=[O:21])([O-])=O>CC(C)=O>[F:15][C:2]([F:1])([F:14])[C:3]1[CH:4]=[C:5]([CH:11]=[CH:12][CH:13]=1)[O:6][CH:7]1[CH2:10][N:9]([C:20]([NH2:19])=[O:21])[CH2:8]1

Komponenten

4

Edukt 2

HCID 62372NitroureaHCID 111385383-[3-(Trifluoromethyl)phenoxy]azetidine

Produkt 1

HCID 146291Dezinamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 180AcetoneLösungsmittel

Versuchsvorschrift

A mixture of 30.6 g (0.141 mole) of 3-[3-(trifluoromethyl)phenoxy]azetidine and 42 g (0.321 mole) of nitrourea (80%) in 500 ml of acetone was stirred for 5 days (5 days not required, but convenient) at room temperature. The mixture was filtered and the filtrate concentrated in vacuo. The residue was partitioned between 150 ml of water and 100 ml of ethyl acetate and the layers separated. The aqueous layer was washed with 100 ml of ethyl acetate. The ethyl acetate layers were washed with 75 ml of 5% aqueous sodium hydroxide solution followed by 75 ml of water, dried over sodium sulfate and concentrated in vacuo. The residual oil was crystallized from ethyl alcohol-ethyl acetate to give 22 g (60%) substantially the title compound. Recrystallization twice from ethyl alcohol gave 9.9 g of white crystalline solid, m.p. 151°-152.5° C.

Aufarbeitung

  1. customat room temperature
  2. filtrationThe mixture was filtered
  3. concentrationthe filtrate concentrated in vacuo
  4. customThe residue was partitioned between 150 ml of water and 100 ml of ethyl acetate
  5. customthe layers separated
  6. washThe aqueous layer was washed with 100 ml of ethyl acetate
  7. washThe ethyl acetate layers were washed with 75 ml of 5% aqueous sodium hydroxide solution
  8. dry with materialdried over sodium sulfate
  9. concentrationconcentrated in vacuo
  10. customThe residual oil was crystallized from ethyl alcohol-ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-c8deab93588b4d5995f0d79cf96e7c3e
Quelldatensatz
uspto-grants-1991_11
Patentnummer
US05068231

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