Beteiligte Stoffe
| Rolle | Name | HCID | Einwaage |
|---|
| Edukt | Hydrochloric Acid | HCID 313 | — |
| Edukt | Carbon Disulfide | HCID 6348 | — |
| Edukt | Triethylamine | HCID 8471 | — |
| Edukt | Hydrazine hydrate (1:1) | HCID 24654 | — |
| Edukt | Methyl 3-[4-(methylsulfinyl)phenyl]-1-benzofuran-5-carboxylate | HCID 44482291 | — |
| Lösungsmittel | Ethanol | HCID 702 | — |
| Lösungsmittel | Methanol | HCID 887 | — |
| Lösungsmittel | Water | HCID 962 | — |
| Produkt | HCID 178504596 | HCID 178504596 | 47% |
Reaktionsschritte
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.
Herkunft & Nachweise
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patentnummer | US08492378B2 |
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| Quelldatensatz | uspto-grants-2013_07 |
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| ORD ID | ord-ebd723acf2724f15b0c884783029fd0e |
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| Quellennotiz | uspto-grants-2013_07 |
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