Hydrochloric Acid → HCID 178504596, Verbindung

HRID 452778

Reaktionsgleichung

Reaktionsgleichung von HRID 452778
[CH3:1][S:2]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2[C:14]3[CH:15]=[C:16]([C:19]([O:21]C)=O)[CH:17]=[CH:18][C:13]=3[O:12][CH:11]=2)=[CH:6][CH:5]=1)=[O:3].O.[NH2:24][NH2:25].[C:26](=[S:28])=S.C(N(CC)CC)C.Cl>CO.C(O)C.O>[CH3:1][S:2]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2[C:14]3[CH:15]=[C:16]([C:19]4[O:21][C:26]([SH:28])=[N:25][N:24]=4)[CH:17]=[CH:18][C:13]=3[O:12][CH:11]=2)=[CH:6][CH:5]=1)=[O:3]

Komponenten

9

Edukt 5

HCID 313Hydrochloric AcidHCID 6348Carbon DisulfideHCID 8471TriethylamineHCID 24654Hydrazine hydrate (1:1)HCID 44482291Methyl 3-[4-(methylsulfinyl)phenyl]-1-benzofuran-5-carboxylate

Produkt 1

HCID 178504596HCID 178504596, VerbindungAusbeute 47 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 702EthanolLösungsmittelHCID 887MethanolLösungsmittelHCID 962WaterLösungsmittel

Versuchsvorschrift

A solution of methyl 3-[4-(methylsulfinyl)phenyl]-1-benzofuran-5-carboxylate (2.23 g, 7.10 mmol) and hydrazine monohydrate (1.76 mL, 36.3 mmol) in methanol (25 mL) was heated under reflux for 4 days. After cooling, the reaction mixture was concentrated under reduced pressure, and a solution of the obtained residue, carbon disulfide (1.28 mL, 21.3 mmol) and triethylamine (1.19 mL, 8.52 mmol) in ethanol (30 mL) was heated under reflux for 4 hr. After cooling, the reaction mixture was poured into water, and the mixture was acidified with 1M hydrochloric acid and extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was recrystallized from tetrahydrofuran to give the title compound (1.19 g, yield 47%) as pale-yellow crystals.

Aufarbeitung

  1. temperatureunder reflux for 4 days
  2. temperatureAfter cooling
  3. concentrationthe reaction mixture was concentrated under reduced pressure
  4. temperatureunder reflux for 4 hr
  5. temperatureAfter cooling
  6. extractionextracted with ethyl acetate
  7. washThe organic layer was washed with saturated brine
  8. dry with materialdried over anhydrous magnesium sulfate
  9. concentrationconcentrated under reduced pressure
  10. customThe residue was recrystallized from tetrahydrofuran

Quellen und Nachweise

ORD-Eintrag
ord-ebd723acf2724f15b0c884783029fd0e
Quelldatensatz
uspto-grants-2013_07
Patentnummer
US08492378B2

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