Benzoyl chloride → 3-Benzoyl-4,5-dimethylthiophene-2-carboxylic acid methylamide

HRID 1744902Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1744902
[CH3:1][NH:2][C:3]([C:5]1[S:6][C:7]([CH3:11])=[C:8]([CH3:10])[CH:9]=1)=[O:4].C([Li])(C)(C)C.[C:17](Cl)(=[O:24])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>C1COCC1>[CH3:1][NH:2][C:3]([C:5]1[S:6][C:7]([CH3:11])=[C:8]([CH3:10])[C:9]=1[C:17](=[O:24])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)=[O:4]

Komponenten

5

Edukt 3

HCID 7412Benzoyl chlorideHCID 11105777HCID 11105777, VerbindungHCID 178418306HCID 178418306, Verbindung

Produkt 1

HCID 110439513-Benzoyl-4,5-dimethylthiophene-2-carboxylic acid methylamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A solution of 10 (0.40 g, 2.37 mmole) in 20 mL dry THF was cooled to −70° C. and stirred during the addition of t-butyllithium (5.21 mmole). After 30 minutes of stirring benzoyl chloride (0.42 g=0.35 mL, 3 mmole) was added and the mixture was warmed to room temperature. Workup consisted of quenching the reaction with saturated aqueous NH4Cl and extraction of product into ethyl acetate. The extract was dried over MgSO4, evaporated and product purified by chromatography on silica gel eluted with hexane-ethyl acetate 1:1. Yield 0.356 g, 55% 1H NMR(CDCl3) δ: 1.83 (s, 3H, CH3), 2.37 (s, 3H, CH3), 2.79 (d, 3H, NHCH3), 6.58 (br s, 1H, NH), 7.42–7.78 (m, 5H, ArH).

Aufarbeitung

  1. customof quenching
  2. customthe reaction
  3. extractionwith saturated aqueous NH4Cl and extraction of product into ethyl acetate
  4. dry with materialThe extract was dried over MgSO4
  5. customevaporated
  6. customproduct purified by chromatography on silica gel
  7. washeluted with hexane-ethyl acetate 1:1

Quellen und Nachweise

ORD-Eintrag
ord-ba64bfb7471c43ee90766f6085678886
Quelldatensatz
uspto-grants-2006_03
Patentnummer
US07019027B2

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