4-Toluenesulfonyl chloride → 3-(Dimethylamino)propyl 4-methylbenzene-1-sulfonate

HRID 1667744Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1667744
[CH3:1][N:2]([CH3:7])[CH2:3][CH2:4][CH2:5][OH:6].[C:8]1([CH3:18])[CH:13]=[CH:12][C:11]([S:14](Cl)(=[O:16])=[O:15])=[CH:10][CH:9]=1>CN(C)C1C=CN=CC=1.N1C=CC=CC=1>[CH3:1][N:2]([CH3:7])[CH2:3][CH2:4][CH2:5][O:6][S:14]([C:11]1[CH:12]=[CH:13][C:8]([CH3:18])=[CH:9][CH:10]=1)(=[O:16])=[O:15]

Komponenten

5

Edukt 2

HCID 73974-Toluenesulfonyl chlorideHCID 766463-(Dimethylamino)-1-propanol

Produkt 1

HCID 214550723-(Dimethylamino)propyl 4-methylbenzene-1-sulfonateAusbeute 16,5 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 1049PyridineLösungsmittel

Versuchsvorschrift

To a mixture of 0.206 g (2 mmole) of 3-dimethylamino-propan-1-ol, and 2 mL of pyridine (2 ml) was added 0.001 g of 4-dimethylaminopyridine and 0.381 g (2 mmole) of p-toluenesulphonyl chloride. The mixture was stirred at ambient temperature overnight and then concentrated under reduced pressure. The residue was taken up in 10 mL of dichloromethane and washed once with 5 mL of saturated sodium bicarbonate, twice with 5 mL of water, and then brine, dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure to give 0.085 g of toluene-4-sulfonic acid 3-dimethylamino-propyl ester as a colorless oil.

Aufarbeitung

  1. concentrationconcentrated under reduced pressure
  2. washwashed once with 5 mL of saturated sodium bicarbonate, twice with 5 mL of water
  3. dry with materialbrine, dried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-0fa9d824fd8849f696d63375d6468479
Quelldatensatz
uspto-grants-2011_10
Patentnummer
US08044213B2

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