Methyl 3-amino-2-thiophenecarboxylate → Methyl 3-(3-(dimethylcarbamoyl)phenylsulfonamido)thiophene-2-carboxylate

HRID 59761

Reaktionsgleichung

Reaktionsgleichung von HRID 59761
[NH2:1][C:2]1[CH:6]=[CH:5][S:4][C:3]=1[C:7]([O:9][CH3:10])=[O:8].[CH3:11][N:12]([CH3:25])[C:13]([C:15]1[CH:16]=[C:17]([S:21](Cl)(=[O:23])=[O:22])[CH:18]=[CH:19][CH:20]=1)=[O:14]>Cl>[CH3:11][N:12]([CH3:25])[C:13]([C:15]1[CH:16]=[C:17]([S:21]([NH:1][C:2]2[CH:6]=[CH:5][S:4][C:3]=2[C:7]([O:9][CH3:10])=[O:8])(=[O:23])=[O:22])[CH:18]=[CH:19][CH:20]=1)=[O:14]

Komponenten

4

Edukt 2

HCID 89652Methyl 3-amino-2-thiophenecarboxylateHCID 180721433-(Dimethylcarbamoyl)benzene-1-sulfonyl chloride

Produkt 1

HCID 86703867Methyl 3-(3-(dimethylcarbamoyl)phenylsulfonamido)thiophene-2-carboxylateAusbeute 91,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 313Hydrochloric AcidLösungsmittel

Versuchsvorschrift

Methyl 3-aminothiophene-2-carboxylate (93 mg, 0.592 mmol) was dissolved in Py (1.5 ml). 3-(dimethylcarbamoyl)benzene-1-sulfonyl chloride (220 mg, 0.887 mmol) was added, and the reaction was stirred at RT for 3 hrs to achieve completion. The reaction mixture was diluted with HCl 1N and extracted with AcOEt. The organic phase was washed with HCl 1N and brine, dried over Na2SO4 and concentrated under vacuum to give methyl 3-(3-(dimethylcarbamoyl)phenylsulfonamido)thiophene-2-carboxylate (Int. 79, 200 mg, 0.543 mmol).

Aufarbeitung

  1. extractionextracted with AcOEt
  2. washThe organic phase was washed with HCl 1N and brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-4b9a69ee2c1049b9bd58d7c8d5660f84
Quelldatensatz
uspto-grants-2016_09
Patentnummer
US09440954B2

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