Triethylamine → 4-Cyanophenethyl methanesulfonate

HRID 1595475Notes

Reaction equation

HRID 1595475 reaction equation
[C:1]([C:3]1[CH:11]=[CH:10][C:6]([CH2:7][CH2:8][OH:9])=[CH:5][CH:4]=1)#[N:2].C(N(CC)CC)C.[CH3:19][S:20](Cl)(=[O:22])=[O:21]>ClCCl>[CH3:19][S:20]([O:9][CH2:8][CH2:7][C:6]1[CH:10]=[CH:11][C:3]([C:1]#[N:2])=[CH:4][CH:5]=1)(=[O:22])=[O:21]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 28008154-(2-Hydroxyethyl)benzonitrile

Product 1

HCID 226326484-Cyanophenethyl methanesulfonateYield 95%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

3.7 g (25 mmole) p-cyanophenethylalcohol was dissolved in 15 ml dichloromethane, 5.2 ml (87.5 mmole) triethylamine was added and the mixture was cooled on an ice bath. 2.52 ml (32.5 mmole) methanesulfonyl chloride in 5 ml dichloromethane was slowly added at 0-7° C. The reaction was allowed to reach room temperature and then stirred at room temperature. The reaction mixture was washed with cooled 2 N hydrochloric acid, water, dried (sodium sulfate), filtered and the solvent was evaporated in vacuo to give 5.3 g (yield 95%) of 4-cyanophenethyl methanesulfonate.

Workup

  1. temperaturethe mixture was cooled on an ice bath
  2. customto reach room temperature
  3. washThe reaction mixture was washed
  4. temperaturewith cooled 2 N hydrochloric acid, water
  5. dry with materialdried (sodium sulfate)
  6. filtrationfiltered
  7. customthe solvent was evaporated in vacuo

Sources & evidence

ORD record
ord-c1f783fa044a4f91b98d4219bbfae856
Source dataset
uspto-grants-2001_09
Patent number
US06288096B1

Reaction notes

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