Methanol → HCID 20032352, Verbindung

HRID 231432Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 231432
[Cl:1][C:2]1[C:7](CO)=[CH:6][C:5]([N:10]2[C:14](=[O:15])[C:13]3[CH2:16][CH2:17][CH2:18][CH2:19][C:12]=3[C:11]2=[O:20])=[C:4]([F:21])[CH:3]=1.[C:22]1([N:28]=[C:29]=[O:30])[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.C(N(CC)CC)C.C[OH:39]>C(OCC)(=O)C>[Cl:1][C:2]1[C:7]([O:30][C:29]([NH:28][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[O:39])=[CH:6][C:5]([N:10]2[C:14](=[O:15])[C:13]3[CH2:16][CH2:17][CH2:18][CH2:19][C:12]=3[C:11]2=[O:20])=[C:4]([F:21])[CH:3]=1

Komponenten

6

Edukt 4

HCID 887MethanolHCID 7672Phenyl isocyanate2×HCID 8471TriethylamineHCID 13629754N-(4-chloro-2-fluoro-5-hydroxymethylphenyl)-3,4,5,6-tetrahydrophthalimide

Produkt 1

HCID 20032352HCID 20032352, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A mixture of 0.5 g (0.0016 mole) of N-(4-chloro-2-fluoro-5-hydroxymethylphenyl]-3,4,5,6-tetrahydrophthalimide, 0.66 g (0.0055 mole) of phenyl isocyanate, 0.73 g (0.0072 mole) of triethylamine, and 25 ml of methylene was stirred at room temperature overnight. Sufficient methanol was added to react with the excess phenyl isocyanate, and the reaction mixture was stirred for an additional 24 hours. The reaction mixture was diluted with ethyl acetate and was washed successively with water and 5% hydrochloric acid. The organic phase was dried, filtered, and the solvent was evaporated under reduced pressure. The residue was passed through a column of silica gel. The appropriate fractions were combined, and the solvent was evaporated under reduced pressure, leaving a white solid as a residue. This solid was recrystallized from ethyl acetate/heptane, yielding 0.29 g of N-[4-chloro-2-fluoro-5-(phenylaminocarbonyloxy)phenyl]-3,4,5,6-tetrahydrophthalimide as a white solid, m.p. 149°-151° C. The nmr and ir spectra were consistent with the proposed structure.

Aufarbeitung

  1. stirringthe reaction mixture was stirred for an additional 24 hours
  2. washwas washed successively with water and 5% hydrochloric acid
  3. customThe organic phase was dried
  4. filtrationfiltered
  5. customthe solvent was evaporated under reduced pressure
  6. customthe solvent was evaporated under reduced pressure
  7. customleaving a white solid as a residue
  8. customThis solid was recrystallized from ethyl acetate/heptane

Quellen und Nachweise

ORD-Eintrag
ord-afeb54faef7449ceaa56a1c6621796f7
Quelldatensatz
uspto-grants-1989_07
Patentnummer
US04846882

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