Benzenesulfonyl chloride → methyl 3-[(phenylsulfonyl)amino]thiophene-2-carboxylate

HRID 1182253Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1182253
[NH2:1][C:2]1[CH:6]=[CH:5][S:4][C:3]=1[C:7]([O:9][CH3:10])=[O:8].[C:11]1([S:17](Cl)(=[O:19])=[O:18])[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1>N1C=CC=CC=1.C(OCC)(=O)C>[CH3:10][O:9][C:7]([C:3]1[S:4][CH:5]=[CH:6][C:2]=1[NH:1][S:17]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)(=[O:19])=[O:18])=[O:8]

Komponenten

5

Edukt 2

HCID 7369Benzenesulfonyl chlorideHCID 89652Methyl 3-amino-2-thiophenecarboxylate

Produkt 1

HCID 4430392methyl 3-[(phenylsulfonyl)amino]thiophene-2-carboxylateAusbeute 92,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 1049PyridineLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

Methyl 3-aminothiophene-2-carboxylate (3.14 g, 20 mmol) was dissolved in pyridine (10 mL) at room temperature. The flask was sealed with a septum and a nitrogen inlet. The solution was treated slowly with a benzenesulfonyl chloride (2.5 mL, 19.5 mmol). The reaction was followed by thin layer chromatography. The reaction was diluted with ethyl acetate and washing with 2N HCl. The organic layer was washed with saturated, aqueous sodium chloride solution and dried over sodium sulfate. The solution was decanted and evaporated under reduced pressure to give 3-benzenesulfonylaminothiophene-2-carboxylic acid methyl ester (5.36 g, 90%), which was used without further purification.

Aufarbeitung

  1. customThe flask was sealed with a septum and a nitrogen inlet
  2. washwashing with 2N HCl
  3. washThe organic layer was washed with saturated, aqueous sodium chloride solution
  4. dry with materialdried over sodium sulfate
  5. customThe solution was decanted
  6. customevaporated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-d4f3f367475f4bfbb0349447e5f88766
Quelldatensatz
uspto-grants-2007_10
Patentnummer
US07288538B2

Notizen zur Reaktion

Wird geladen…