Hydrochloric Acid → HCID 88592485, Verbindung

HRID 531159Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 531159
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([CH2:10][CH:11]([CH2:14][OH:15])[CH2:12][OH:13])=[CH:6][CH:5]=1)([O-:3])=[O:2].[C:16]1([CH3:26])[CH:21]=[CH:20][C:19]([S:22](Cl)(=[O:24])=[O:23])=[CH:18][CH:17]=1.Cl>N1C=CC=CC=1>[CH3:26][C:16]1[CH:21]=[CH:20][C:19]([S:22]([O:13][CH2:12][CH:11]([CH2:10][C:7]2[CH:6]=[CH:5][C:4]([N+:1]([O-:3])=[O:2])=[CH:9][CH:8]=2)[CH2:14][O:15][S:22]([C:19]2[CH:20]=[CH:21][C:16]([CH3:26])=[CH:17][CH:18]=2)(=[O:24])=[O:23])(=[O:24])=[O:23])=[CH:18][CH:17]=1

Komponenten

5

Edukt 3

HCID 313Hydrochloric AcidHCID 73974-Toluenesulfonyl chlorideHCID 23366071HCID 23366071, Verbindung

Produkt 1

HCID 88592485HCID 88592485, VerbindungAusbeute 89 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1049PyridineLösungsmittel2×

Versuchsvorschrift

A solution of 24 (6.43 g, 30.44 mmol) in pyridine (20 mL) was added dropwise to a solution of p-toluenesulfonyl chloride (14.51 g, 76.11 mmol) in pyridine (30 mL), with temperature being kept below 0° C. After complete addition, the reaction mixture was stirred at room temperature for 10 hours, and then it was poured into ice-cold aqueous 5 M HCl (100 mL). The aqueous phase was extracted with CH2Cl2 (3×100 mL). The combined organic phase was washed with brine (2×100 mL), dried over MgSO4, and evaporated under reduced pressure to afford pale yellow oil, which was crystallized from ethanol (100 mL) to give white solid 25 (14.08 g, 89% yield).

Aufarbeitung

  1. custombeing kept below 0° C
  2. additionAfter complete addition
  3. extractionThe aqueous phase was extracted with CH2Cl2 (3×100 mL)
  4. washThe combined organic phase was washed with brine (2×100 mL)
  5. dry with materialdried over MgSO4
  6. customevaporated under reduced pressure
  7. customto afford pale yellow oil, which
  8. customwas crystallized from ethanol (100 mL)

Quellen und Nachweise

ORD-Eintrag
ord-85c6adeba5fd4c449b596d7bca67fe17
Quelldatensatz
uspto-grants-2016_05
Patentnummer
US09353120B2

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