Ethanol → N,N-dimethyl-N'-[2-(4-methylphenyl)phenyl]sulfonylmethanimidamide

HRID 447223

Reaktionsgleichung

Reaktionsgleichung von HRID 447223
Br[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[S:8](/[N:11]=[CH:12]/[N:13]([CH3:15])[CH3:14])(=[O:10])=[O:9].[CH3:16][C:17]1[CH:22]=[CH:21][C:20](B(O)O)=[CH:19][CH:18]=1.C(=O)([O-])[O-].[K+].[K+].CCO.C1(C)C=CC=CC=1>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.CCOC(C)=O.O>[CH3:14][N:13]([CH3:15])/[CH:12]=[N:11]/[S:8]([C:3]1[C:2]([C:20]2[CH:21]=[CH:22][C:17]([CH3:16])=[CH:18][CH:19]=2)=[CH:7][CH:6]=[CH:5][CH:4]=1)(=[O:10])=[O:9]

Komponenten

9

Edukt 5

HCID 702EthanolHCID 1140TolueneHCID 11430Potassium CarbonateHCID 79799Tolylboronic acidHCID 11779014N'-(2-bromophenyl)sulfonyl-N,N-dimethylmethanimidamide

Produkt 1

HCID 9972170N,N-dimethyl-N'-[2-(4-methylphenyl)phenyl]sulfonylmethanimidamideAusbeute 82,7 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 962WaterLösungsmittel2×HCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

2-Bromo-N-[1-dimethylaminometh-(E)-ylidene]-benzenesulfonamide (5.4 g, 18.4 mmol), 4-methylphenylboronic acid (5.0 g, 36.8 mmol) and potassium carbonate (5.1 g, 36.8 mmol) were dissolved in water (19.7 mL, 1090 mmol), EtOH (49.2 mL, 842 mmol) and toluene (98.3 mL, 923 mmol). The resulting mixture was stirred under nitrogen. Tetrakis(triphenylphosphine)palladium(0) (1.4 g, 1.2 mmol) was added. The mixture was heated at 60° C. for 115 minutes, at 70° C. for 30 minutes, then cooled to room temperature. Water (100 mL) and EtOAc (100 mL) were added. The mixture was washed with saturated aqueous NaCl, extracted with EtOAc, dried over MgSO4, filtered, and concentrated to yield a red solid. The product was triturated with 1:1 EtOAc:hexanes, filtered, and rinsed with hexanes to yield a reddish-brown solid. The product was triturated with EtOAc, filtered, and rinsing with EtOAc. to yield 4′-methylbiphenyl-2-sulfonic acid 1-dimethylaminometh-(E)-ylideneamide (4.6 g) as a light brown solid.

Aufarbeitung

  1. temperaturecooled to room temperature
  2. washThe mixture was washed with saturated aqueous NaCl
  3. extractionextracted with EtOAc
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto yield a red solid
  8. customThe product was triturated with 1:1 EtOAc
  9. filtrationhexanes, filtered
  10. washrinsed with hexanes
  11. customto yield a reddish-brown solid
  12. customThe product was triturated with EtOAc
  13. filtrationfiltered
  14. washrinsing with EtOAc

Quellen und Nachweise

ORD-Eintrag
ord-b664500bc7d24b0fa37653e2d91d2d60
Quelldatensatz
uspto-grants-2013_07
Patentnummer
US08481549B2

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