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Triethylamine → HCID 20800560, Verbindung

HRID 1071518
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1071518
[OH:1][CH2:2][CH:3]([N:10]1[CH2:18][C:17]2[C:12](=[CH:13][CH:14]=[C:15]([CH3:19])[CH:16]=2)[C:11]1=[O:20])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.C(N(CC)CC)C.[CH3:28][S:29](Cl)(=[O:31])=[O:30].C(=O)(O)[O-].[Na+]>C(Cl)Cl>[CH3:19][C:15]1[CH:16]=[C:17]2[C:12](=[CH:13][CH:14]=1)[C:11](=[O:20])[N:10]([CH:3]([C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1)[CH2:2][O:1][S:29]([CH3:28])(=[O:31])=[O:30])[CH2:18]2
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 516892Sodium BicarbonateHCID 22393547HCID 22393547, Verbindung

Produkt 1

HCID 20800560HCID 20800560, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344Dichloromethane
Lösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

2-(2-Hydroxy-1-phenyl-ethyl)-5-methyl-2,3-dihydro-isoindol-1-one (4.72 g, 17.66 mmol) and triethylamine (5.36 g, 53.97 mmol, 7.38 mL) were taken up in anhydrous DCM (50 mL), under argon and cooled to 0° C. Methanesulfonyl chloride (2.22 g, 19.43 mmol, 1.5 mL) was added to the reaction over 10 min. The reaction was stirred for 1 h at 0° C. then allowed to slowly warm to room temp and stirred for 4 h. The reaction was slowly poured into saturated sodium bicarbonate and the aqueous layer was extracted three times with ethyl acetate. The combined organic layers were washed with 1N HCl, water, brine and dried over anhydrous magnesium sulfate. The solution was filtered and the solvent removed under reduced pressure. The product was used in the next step without further purification. Yield 5.61 g.

Aufarbeitung

  1. temperatureto slowly warm to room temp
  2. stirringstirred for 4 h
  3. extractionthe aqueous layer was extracted three times with ethyl acetate
  4. washThe combined organic layers were washed with 1N HCl, water, brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationThe solution was filtered
  7. customthe solvent removed under reduced pressure
  8. customThe product was used in the next step without further purification

Quellen und Nachweise

ORD-Eintrag
ord-ec3d3b3e1691428f84030a62b496d09e
Quelldatensatz
uspto-grants-2005_06
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06906067B2

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