Methyl Isocyanate → HCID 20074956, Verbindung

HRID 703824Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 703824
[C:1]([C:3]1[CH:4]=[C:5]([N:9]([CH2:11][C:12]([O:14]C)=O)[NH2:10])[CH:6]=[CH:7][CH:8]=1)#[N:2].[CH3:16][N:17]=[C:18]=[O:19]>C(#N)C>[C:1]([C:3]1[CH:4]=[C:5]([N:9]2[CH2:11][C:12](=[O:14])[N:17]([CH3:16])[C:18](=[O:19])[NH:10]2)[CH:6]=[CH:7][CH:8]=1)#[N:2]

Komponenten

4

Edukt 2

HCID 12228Methyl IsocyanateHCID 54460083HCID 54460083, Verbindung

Produkt 1

HCID 20074956HCID 20074956, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

Methyl [1-(3-cyanophenyl)hydrazino]acetate (700 mg) was dissolved in dry acetonitrile (10 ml) under nitrogen. Methyl isocyanate (0.7 ml) was added to the reaction mixture which was then heated at reflux for 1.5 h. The solvent was removed in vacuo and the oily residue was dissolved in methanol (10 ml) under nitrogen. Sodium methoxide (2.17M solution in methanol; 3.9 ml) was added and the solution was stirred at room temperature for 2 h. The reaction was poured into pH 6.5 phosphate buffer (100 ml) and extracted with ethyl acetate (3×80 ml). The combined, dried organic extracts were concentrated at reduced pressure to give a solid which was triturated with ether (3×20 ml) to give the title compound (640 mg), m.p. 174°-178°. N.m.r. indicated 0.084 mol ethyl acetate.

Aufarbeitung

  1. temperaturewas then heated
  2. temperatureat reflux for 1.5 h
  3. customThe solvent was removed in vacuo
  4. dissolutionthe oily residue was dissolved in methanol (10 ml) under nitrogen
  5. additionSodium methoxide (2.17M solution in methanol; 3.9 ml) was added
  6. additionThe reaction was poured into pH 6.5 phosphate buffer (100 ml)
  7. extractionextracted with ethyl acetate (3×80 ml)
  8. concentrationdried organic extracts were concentrated at reduced pressure
  9. customto give a solid which
  10. customwas triturated with ether (3×20 ml)

Quellen und Nachweise

ORD-Eintrag
ord-b13d63bcd9134f4f83c834b5e33b3d1d
Quelldatensatz
uspto-grants-1991_01
Patentnummer
US04985427

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