N-methyl-N-methoxy-2-chloro-5-sulfamoylthiophene-3-carboxamide → 4-Acetyl-5-chlorothiophene-2-sulfonamide
Reaktionsgleichung
C[Li].[CH3:3]COCC.CN(OC)[C:10]([C:12]1[CH:16]=[C:15]([S:17](=[O:20])(=[O:19])[NH2:18])[S:14][C:13]=1[Cl:21])=[O:11]>C1COCC1>[C:10]([C:12]1[CH:16]=[C:15]([S:17]([NH2:18])(=[O:20])=[O:19])[S:14][C:13]=1[Cl:21])(=[O:11])[CH3:3]Komponenten
4
Edukt 2
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Reaktionsbedingungen
- Temperatur
- -78 °C
Versuchsvorschrift
A solution of 1.5M methyllithium/ether (26 mL, 0.039 mol) was added dropwise to a solution of N-methyl-N-methoxy-2-chloro-5-sulfamoylthiophene-3-carboxamide (3.25 g, 0.011 mol) in dry THF (145 mL) under a nitrogen atmosphere, cooled to -78° C. After two hours, the reaction mixture was poured carefully into ice/dil. HCl and the product was extracted into ethyl acetate. This extract was washed with water and brine, dried (Na2SO4), filtered and evaporated to give 2.82 g of crude solid product. This material was chromatographed on silica gel and eluted with 40% ethyl acetate/hexane to give 1.7 g (74%) of product. Recrystallization from ethyl acetate/hexane gave 1.68 g of product, mp 128°-130° C.
Aufarbeitung
- additionthe reaction mixture was poured carefully into ice/dil
- extractionHCl and the product was extracted into ethyl acetate
- washThis extract was washed with water and brine
- dry with materialdried (Na2SO4)
- filtrationfiltered
- customevaporated
- customto give 2.82 g of crude solid product
- customThis material was chromatographed on silica gel
- washeluted with 40% ethyl acetate/hexane
Quellen und Nachweise
- ORD-Eintrag
- ord-a0902973f10e4932823b0ae2b6ca229c
- Quelldatensatz
- uspto-grants-1994_01
- Patentnummer
- US05276025
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