Toluene → 2'-Sulfamoyl-biphenyl-4-carboxylic acid

HRID 1392787Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1392787
Br[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[S:8]([NH2:11])(=[O:10])=[O:9].[C:12]([C:15]1[CH:20]=[CH:19][C:18](B(O)O)=[CH:17][CH:16]=1)([OH:14])=[O:13].C1(C)C=CC=CC=1.C(=O)([O-])[O-].[Na+].[Na+]>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.O.C(OCC)C>[NH2:11][S:8]([C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[C:18]1[CH:19]=[CH:20][C:15]([C:12]([OH:14])=[O:13])=[CH:16][CH:17]=1)(=[O:10])=[O:9]

Komponenten

8

Edukt 4

HCID 1140TolueneHCID 10340Sodium CarbonateHCID 3121834-Carboxyphenylboronic AcidHCID 28012632-Bromobenzenesulfonamide

Produkt 1

HCID 27605552'-Sulfamoyl-biphenyl-4-carboxylic acidAusbeute 57,4 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 962WaterLösungsmittel2×HCID 3283Diethyl EtherLösungsmittel

Versuchsvorschrift

2-Bromobenzenesulfonamide (800 mg) and 4-carboxyphenylboronic acid (563 mg) were suspended in a mixed solvent of toluene (5 ml) and water (5 ml). Tetrakis(triphenylphosphine)palladium (392 mg) and anhydrous sodium carbonate (1.08 g) were successively added to the suspension, and the mixture was heated under reflux overnight. After the reaction mixture was cooled to room temperature, diethyl ether and water were added to conduct liquid separation. The resultant organic layer was extracted twice with water. The resultant water layers were all combined, and 12N hydrochloric acid was added to this solution to acidify it. The solution was concentrated to about 20 ml under reduced pressure. Colorless powder deposited was collected by filtration and dried under reduced pressure to obtain the title compound (539 mg).

Aufarbeitung

  1. temperaturethe mixture was heated
  2. temperatureunder reflux overnight
  3. customliquid separation
  4. extractionThe resultant organic layer was extracted twice with water
  5. addition12N hydrochloric acid was added to this solution
  6. concentrationThe solution was concentrated to about 20 ml under reduced pressure
  7. filtrationColorless powder deposited was collected by filtration
  8. customdried under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-bc99965c81c849a19ec6aa2d5ce765e5
Quelldatensatz
uspto-grants-2008_03
Patentnummer
US07342014B2

Notizen zur Reaktion

Wird geladen…