(2-(Methylthio)ethyl)amine → 3-Chloro-1-[2-(methylsulfanyl)ethyl]-4-phenyl-1H-pyrrole-2,5-dione

HRID 2113746Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2113746
[Cl:1][C:2]1[C:3](=[O:14])O[C:5](=[O:13])[C:6]=1[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.[CH3:15][S:16][CH2:17][CH2:18][NH2:19]>C(O)(=O)C>[Cl:1][C:2]1[C:3](=[O:14])[N:19]([CH2:18][CH2:17][S:16][CH3:15])[C:5](=[O:13])[C:6]=1[C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=1

Komponenten

4

Edukt 2

HCID 87697(2-(Methylthio)ethyl)amineHCID 234471953-Chloro-4-phenylfuran-2,5-dione

Produkt 1

HCID 691478763-Chloro-1-[2-(methylsulfanyl)ethyl]-4-phenyl-1H-pyrrole-2,5-dioneAusbeute 54 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 176Acetic AcidLösungsmittel

Versuchsvorschrift

A solution of 3-chloro-4-phenylfuran-2,5-dione (1.00 mmol, 209 mg) and 2-aminoethyl methyl sulphide (1.00 mmol, 91 mg) in glacial acetic acid (2 mL) was heated in a microwave reactor at 120° C. for two min. After cooling, the solvent was evaporated at reduced pressure. The residue was partitioned between water and CH2Cl2. The organic phase was evaporated and the crude product was purified by HPLC (95% 0.1M ammonium acetate buffer: 5% CH3CN→100% CH3CN) to give 152 mg (54%) of the title compound. 1H NMR (400 MHz, CDCl3): δ 7.97-7.90 (m, 2H), 7.53-7.47 (m, 3H), 3.86 (t, J=6.8 Hz, 2H), 2.78 (t, J=6.8 Hz, 2H), 2.16 (s, 3H).

Aufarbeitung

  1. temperatureAfter cooling
  2. customthe solvent was evaporated at reduced pressure
  3. customThe residue was partitioned between water and CH2Cl2
  4. customThe organic phase was evaporated
  5. customthe crude product was purified by HPLC (95% 0.1M ammonium acetate buffer: 5% CH3CN→100% CH3CN)

Quellen und Nachweise

ORD-Eintrag
ord-2babcd1b89fb4a15bf99ed12987f76c0
Quelldatensatz
uspto-grants-2008_10
Patentnummer
US07432288B2

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