N-Methylphenylethanolamine → HCID 21842621, Verbindung

HRID 1737450

Reaktionsgleichung

Reaktionsgleichung von HRID 1737450
[CH3:1][NH:2][CH2:3][CH:4]([OH:11])[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.[C:12]1([S:18](Cl)(=[O:20])=[O:19])[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C(N(CC)C(C)C)(C)C>C1COCC1>[OH:11][CH:4]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)[CH2:3][N:2]([CH3:1])[S:18]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)(=[O:20])=[O:19]

Komponenten

5

Edukt 3

HCID 913N-MethylphenylethanolamineHCID 7369Benzenesulfonyl chlorideHCID 81531Diisopropylethylamine

Produkt 1

HCID 21842621HCID 21842621, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A solution of α-(methylaminomethyl)benzyl alcohol (1.00 g, 6.61 mmol) in 15 mL of THF was cooled in an ice bath. Benzenesulfonyl chloride (0.886 mL, 1.23 g, 6.94 mmol) and N,N-diisopropylethylamine (2.3 mL, 1.7 g, 13 mmol) were added and mixture was allowed to warm to room temperature. After 30 min, the solvent was evaporated and the residue was partitioned between 50 mL of ethyl acetate and 40 mL of saturated aqueous sodium bicarbonate. The aqueous layer was extracted with 2×50 mL of ethyl acetate. The combined organic layers were washed with 50 mL of brine, dried over sodium sulfate, and evaporated. Purification by flash column chromatography on silica gel, eluting with 20-50% ethyl acetate in hexane, gave the title compound in quantitative yield.

Aufarbeitung

  1. customthe solvent was evaporated
  2. customthe residue was partitioned between 50 mL of ethyl acetate and 40 mL of saturated aqueous sodium bicarbonate
  3. extractionThe aqueous layer was extracted with 2×50 mL of ethyl acetate
  4. washThe combined organic layers were washed with 50 mL of brine
  5. dry with materialdried over sodium sulfate
  6. customevaporated
  7. customPurification by flash column chromatography on silica gel
  8. washeluting with 20-50% ethyl acetate in hexane

Quellen und Nachweise

ORD-Eintrag
ord-ba598985bff041bf90162b74bd66b628
Quelldatensatz
uspto-grants-1999_10
Patentnummer
US05962462

Verknüpfte Notizen

Wird geladen…