Sodium methanethiolate → 5-Methoxy-3-(methylthio)benzo[b]thiophene-2-carboxamide

HRID 2226853Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2226853
[CH3:1][S-:2].[Na+].Cl[C:5]1[C:6]2[CH:16]=[C:15]([O:17][CH3:18])[CH:14]=[CH:13][C:7]=2[S:8][C:9]=1[C:10]([NH2:12])=[O:11]>CN(C=O)C.C(OCC)(=O)C>[CH3:18][O:17][C:15]1[CH:14]=[CH:13][C:7]2[S:8][C:9]([C:10]([NH2:12])=[O:11])=[C:5]([S:2][CH3:1])[C:6]=2[CH:16]=1

Komponenten

5

Edukt 2

HCID 4378561Sodium methanethiolate2×HCID 106815953-Chloro-5-methoxybenzo[b]thiophene-2-carboxamide

Produkt 1

HCID 108247755-Methoxy-3-(methylthio)benzo[b]thiophene-2-carboxamideAusbeute 72 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

Sodium thiomethoxide (93 mg, 1.32 mmol) is added to a suspension of 3-chloro-5-methoxybenzo[b]thiophene-2-carboxamide (250 mg, 1.03 mmol) in 2 mL of DMF. After 1 hour, an additional amount of sodium thiomethoxide (13 mg) is added. The reaction mixture is diluted with ethyl acetate and washed with 1N NaOH, 1N HCl, water, and brine. The organic layer is dried over MgSO4. Filtration followed by concentration in vacuo and recrystallization from ethyl acetate:hexane gives 5-methoxy-3-(methylthio)benzo[b]thiophene-2-carboxamide in 72% yield; mp=171°-173° C.

Aufarbeitung

  1. washwashed with 1N NaOH, 1N HCl, water, and brine
  2. dry with materialThe organic layer is dried over MgSO4
  3. filtrationFiltration
  4. concentrationfollowed by concentration in vacuo and recrystallization from ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-ba72a96911714921855ee1f0c6826876
Quelldatensatz
uspto-grants-1994_09
Patentnummer
US05350748

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