Dimethyl acetylenedicarboxylate → HCID 178418430, Verbindung

HRID 3105

Reaktionsgleichung

Reaktionsgleichung von HRID 3105
[NH2:1][C:2]1[CH:11]=[C:10]([Cl:12])[CH:9]=[C:8]([Cl:13])[C:3]=1[C:4]([O:6]C)=O.[C:14]([C:20]([O:22][CH3:23])=[O:21])#[C:15][C:16]([O:18][CH3:19])=[O:17].CC(C)([O-])C.[K+]>C(O)(C)(C)C>[Cl:13][C:8]1[CH:9]=[C:10]([Cl:12])[CH:11]=[C:2]2[C:3]=1[C:4]([OH:6])=[C:14]([C:20]([O:22][CH3:23])=[O:21])[C:15]([C:16]([O:18][CH3:19])=[O:17])=[N:1]2

Komponenten

5

Edukt 3

HCID 12980Dimethyl acetylenedicarboxylateHCID 12363232Methyl 2-amino-4,6-dichlorobenzoateHCID 23665647Potassium tert-butoxide

Produkt 1

HCID 178418430HCID 178418430, VerbindungAusbeute 59 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6386tert-ButanolLösungsmittel

Versuchsvorschrift

A solution of methyl 2-amino-4,6-dichlorobenzoate (1.30 g, 5.91 mM) and dimethyl acetylenedicarboxylate (0.96 g, 6.78 mM) in t-butanol (14 mL) was refluxed for 18 hr under a nitrogen atmosphere. The reaction mixture was cooled to room temperature and potassium t-butoxide (0.76 g, 6.8 mM) was added to the stirred mixture whereupon a precipitate formed. After refluxing for 1.5 hr, the reaction mixture was cooled to room temperature and filtered to separate the precipitated solids. The solids were washed with t-butanol and then dissolved in water. The resulting solution was acidified with 1N H2SO4 and the resulting precipitate was collected, washed thoroughly with water and dried to give the title compound as a light green solid (1.15 g, 59%). An analytical sample was obtained by recrystallization of a portion from toluene to provide the title compound as a light tan solid, mp 109.5°-111° C. (d); MS(CI): 330 (M+H).

Aufarbeitung

  1. customformed
  2. temperatureAfter refluxing for 1.5 hr
  3. temperaturethe reaction mixture was cooled to room temperature
  4. filtrationfiltered
  5. customto separate the precipitated solids
  6. washThe solids were washed with t-butanol
  7. dissolutiondissolved in water
  8. customthe resulting precipitate was collected
  9. washwashed thoroughly with water
  10. customdried

Quellen und Nachweise

ORD-Eintrag
ord-80b7e4ba59954100866003a993d7b735
Quelldatensatz
uspto-grants-1998_03
Patentnummer
US05733910

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