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

HRID 33491Notes

Reaction equation

HRID 33491 reaction equation
[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

Participants

7

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent3×

Conditions

Temperature
-4 °C

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-3076a8092c6b42be9a06233e1c44028f
Source dataset
uspto-grants-2008_09
Patent number
US07429605B2

Reaction notes

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