Hydrochloric Acid → 2-(1H-1,2,3-triazol-1-yl)ethyl 4-methyl-1-benzenesulfonate

HRID 750964

Reaktionsgleichung

Reaktionsgleichung von HRID 750964
[C:1]1([CH3:11])[CH:6]=[CH:5][C:4]([S:7](Cl)(=[O:9])=[O:8])=[CH:3][CH:2]=1.C(N(CC)CC)C.[N:19]1([CH2:24][CH2:25][OH:26])[CH:23]=[CH:22][N:21]=[N:20]1.Cl>CN(C1C=CN=CC=1)C.ClCCl>[N:19]1([CH2:24][CH2:25][O:26][S:7]([C:4]2[CH:5]=[CH:6][C:1]([CH3:11])=[CH:2][CH:3]=2)(=[O:9])=[O:8])[CH:23]=[CH:22][N:21]=[N:20]1

Komponenten

7

Edukt 4

HCID 313Hydrochloric AcidHCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 99892372-(1H-1,2,3-triazol-1-yl)ethan-1-ol

Produkt 1

HCID 226671112-(1H-1,2,3-triazol-1-yl)ethyl 4-methyl-1-benzenesulfonate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 6344DichloromethaneLösungsmittel3×

Reaktionsbedingungen

Temperatur
-4 °C

Versuchsvorschrift

A solution of 12.9 g (66.3 mmol) p-toluenesulfonic acid chloride, 2.03 g (16.6 mmol) 4-(N,N-dimethylamino)-pyridine and 11.2 ml (80.2 mmol) triethylamine in 150 ml dichloromethane was cooled to -10° C. A solution of 7.50 g (66.3 mmol) 2-(1H-[1,2,3]triazol-1-yl)-ethanol in 150 ml dichloromethane was added dropwise and the mixture stirred overnight at -4° C. 170 ml Ice and 170 ml dichloromethane were added and stirring continued for 10 min. followed by addition of 3.9 ml conc. HCl. The organic phase was separated, washed with sat. NaHCO3-solution and brine, dried over Na2SO4 and solvents distilled off. Yield 15.3 g (86%) orange crystals.

Aufarbeitung

  1. stirringstirring
  2. waitcontinued for 10 min.
  3. customThe organic phase was separated
  4. washwashed with sat. NaHCO3-solution and brine
  5. dry with materialdried over Na2SO4 and solvents
  6. distillationdistilled off

Quellen und Nachweise

ORD-Eintrag
ord-a558f23d58d24facbe2f087962a594fb
Quelldatensatz
uspto-grants-2008_07
Patentnummer
US07405231B2

Verknüpfte Notizen

Wird geladen…