Triethylamine → 2-Cyano-2-(4-chlorophenyl)propyl methane sulfonate

HRID 28261Notes

Reaction equation

HRID 28261 reaction equation
[C:1]([C:3]([C:7]1[CH:12]=[CH:11][C:10]([Cl:13])=[CH:9][CH:8]=1)([CH3:6])[CH2:4][OH:5])#[N:2].[CH3:14][S:15](Cl)(=[O:17])=[O:16].C(N(CC)CC)C>C1C=CC=CC=1>[CH3:14][S:15]([O:5][CH2:4][C:3]([C:1]#[N:2])([C:7]1[CH:8]=[CH:9][C:10]([Cl:13])=[CH:11][CH:12]=1)[CH3:6])(=[O:17])=[O:16]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 140328512-Cyano-2-(4-chlorophenyl)propan-1-ol

Product 1

HCID 233398692-Cyano-2-(4-chlorophenyl)propyl methane sulfonate

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

To a mixture of 2-cyano-2-(4-chlorophenyl)propan-1-ol (68 g., 0.3 mole) and methane sulfonyl chloride (37.5 g., 0.33 mole) in 2 liters of benzene is added dropwise at 10° C., 36 g., (0.36 mole) of triethylamine. The reaction mixture is stirred at room temperature for 30 minutes and then heated on a steam bath for another 30 minutes. The precipitate formed is filtered and the filtrate is washed with dilute hydrochloric acid, water, saturated sodium bicarbonate solution, saturated sodium chloride solution and dried over magnesium sulfate. The solvent is evaporated to give 63 g. of product.

Workup

  1. additionis added dropwise at 10° C.
  2. temperatureheated on a steam bath for another 30 minutes
  3. customThe precipitate formed
  4. filtrationis filtered
  5. washthe filtrate is washed with dilute hydrochloric acid, water, saturated sodium bicarbonate solution, saturated sodium chloride solution
  6. dry with materialdried over magnesium sulfate
  7. customThe solvent is evaporated
  8. customto give 63 g

Sources & evidence

ORD record
ord-387eb2201a9f4d359e4f909017ff1dad
Source dataset
uspto-grants-1980_09
Patent number
US04225723

Reaction notes

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