Hydrochloric Acid → 5-(4-Chlorophenyl)-4-((dimethylamino)methyl)-3-(4sulfamoylphenyl) thiophene-2-carboxylic acid

HRID 1053265Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1053265
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[S:12][C:11]([C:13]([O:15]CC)=[O:14])=[C:10]([C:18]3[CH:23]=[CH:22][C:21]([S:24](=[O:31])(=[O:30])[N:25]=CN(C)C)=[CH:20][CH:19]=3)[C:9]=2[CH2:32][N:33]([CH3:35])[CH3:34])=[CH:4][CH:3]=1.[OH-].[Na+].Cl>C(O)C.O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[S:12][C:11]([C:13]([OH:15])=[O:14])=[C:10]([C:18]3[CH:23]=[CH:22][C:21]([S:24](=[O:30])(=[O:31])[NH2:25])=[CH:20][CH:19]=3)[C:9]=2[CH2:32][N:33]([CH3:35])[CH3:34])=[CH:6][CH:7]=1

Komponenten

6

Edukt 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 68285447Ethyl 5-(4-chlorophenyl)-4-((dimethylamino)methyl)-3-(4-(N-((dimethylamino)methylene)sulfamoyl)phenyl)thiophene-2-carboxylate2×

Produkt 1

HCID 682862315-(4-Chlorophenyl)-4-((dimethylamino)methyl)-3-(4sulfamoylphenyl) thiophene-2-carboxylic acidAusbeute 94,9 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 702EthanolLösungsmittelHCID 962WaterLösungsmittel2×

Reaktionsbedingungen

Temperatur
75 °C

Versuchsvorschrift

Ethyl 5-(4-chlorophenyl)-4-((dimethylamino)methyl)-3-(4-(N-((dimethylamino)methylene)sulfamoyl)phenyl)thiophene-2-carboxylate (compound 35c, 1.0 g, 1.87 mmol) was suspended in ethanol (20 ml) and a solution of NaOH (0.37 g, 9.36 mmol) in water (2 ml) was added to it at 25° C. The reaction mixture was heated at 75° C. under stirring for 2 hr. The progress of the reaction was monitored by TLC. The reaction mixture was concentrated under reduced pressure. The residue so obtained was then diluted with water (5 ml) and cooled using ice bath. To the cooled mixture was then added aqueous 10% HCl to bring pH of the mixture to between 5 and 6. The resulting solid was filtered and dried under reduced pressure to obtain the title compound (0.8 g, 94.78%).

Aufarbeitung

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customThe residue so obtained
  3. temperaturecooled
  4. filtrationThe resulting solid was filtered
  5. customdried under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-ad7dcb8329e944b2a9dc5208f50e845d
Quelldatensatz
uspto-grants-2016_07
Patentnummer
US09393247B2

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