Hydrochloric Acid → N-Cyclohexyl-3-(hydroxymethyl)benzenesulfonamide

HRID 219028

Reaktionsgleichung

Reaktionsgleichung von HRID 219028
[CH:1]1([NH:7][S:8]([C:11]2[CH:12]=[C:13]([CH:17]=[CH:18][CH:19]=2)[C:14](O)=[O:15])(=[O:10])=[O:9])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.B.C1COCC1.CO.Cl>C1COCC1>[CH:1]1([NH:7][S:8]([C:11]2[CH:19]=[CH:18][CH:17]=[C:13]([CH2:14][OH:15])[CH:12]=2)(=[O:9])=[O:10])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 7791083-(Cyclohexylsulfamoyl)benzoic acidHCID 2723981Borane;tetrahydrofuran

Produkt 1

HCID 65751619N-Cyclohexyl-3-(hydroxymethyl)benzenesulfonamideAusbeute 90,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A solution of 3-[(cyclohexylamino)sulfonyl]benzoic acid (2.25 g) in THF (100 ml) under nitrogen at 0° was treated dropwise with 1M borane-THF solution (23.82 ml). The mixture was stirred at 0° for 0.5 h and then at 20° for 72 h. The mixture was cooled to 0° and MeOH (20 ml) was added dropwise. The mixture was stirred for 15 min and then 2N hydrochloric acid (50 ml) was added and the mixture was allowed to warm to 20°. The bulk of the organic solvents were removed by evaporation in vacuo and the residual aqueous phase was extracted with EtOAc (2×40 ml). The combined extracts were dried (Na2SO4) and the solvent evaporated in vacuo. The residue was purified by SPE on alumina (10 g, activated, neutral, Brockmann 1). Elution with MeOH-dichloromethane (1:20) gave the title compound (1.944 g). LCMS RT=2.95 min, ES+ve 270 (MH)+.

Aufarbeitung

  1. waitat 20° for 72 h
  2. temperatureThe mixture was cooled to 0°
  3. stirringThe mixture was stirred for 15 min
  4. temperatureto warm to 20°
  5. customThe bulk of the organic solvents were removed by evaporation in vacuo
  6. extractionthe residual aqueous phase was extracted with EtOAc (2×40 ml)
  7. dry with materialThe combined extracts were dried (Na2SO4)
  8. customthe solvent evaporated in vacuo
  9. customThe residue was purified by SPE on alumina (10 g, activated, neutral, Brockmann 1)
  10. washElution with MeOH-dichloromethane (1:20)

Quellen und Nachweise

ORD-Eintrag
ord-a2efa7f015cb405f968547bf340884f5
Quelldatensatz
uspto-grants-2012_06
Patentnummer
US08198483B2

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