Methanesulfonyl chloride → Methanesulfonic acid 2-methyl-6-(4-trifluoromethyl-phenyl)-pyridin-3-ylmethyl ester

HRID 1242387Notes

Reaction equation

HRID 1242387 reaction equation
[CH3:1][C:2]1[C:7]([CH2:8][OH:9])=[CH:6][CH:5]=[C:4]([C:10]2[CH:15]=[CH:14][C:13]([C:16]([F:19])([F:18])[F:17])=[CH:12][CH:11]=2)[N:3]=1.C(N(C(C)C)C(C)C)C.[CH3:29][S:30](Cl)(=[O:32])=[O:31]>C(Cl)Cl>[CH3:1][C:2]1[C:7]([CH2:8][O:9][S:30]([CH3:29])(=[O:32])=[O:31])=[CH:6][CH:5]=[C:4]([C:10]2[CH:15]=[CH:14][C:13]([C:16]([F:17])([F:19])[F:18])=[CH:12][CH:11]=2)[N:3]=1

Participants

5

Reactant 3

HCID 31297Methanesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 21935862[2-Methyl-6-(4-trifluoromethyl-phenyl)-pyridin-3-yl]-methanol

Product 1

HCID 86597805Methanesulfonic acid 2-methyl-6-(4-trifluoromethyl-phenyl)-pyridin-3-ylmethyl ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

2.60 g (9.7 mmol) of [2-methyl-6-(4-trifluoromethyl-phenyl)-pyridin-3-yl]-methanol (example 1M]) were dissolved in 50 ml MeCl2 and cooled down to 0° C. 2.55 ml=1.93 g (14.6 mmol) of N-ethyl diisopropylamine was added, followed by 0.85 ml=1.25 g (10.7 mmol) of methane sulfonylchloride, drop by drop. After stirring for 30 min. at ambient temperature, the reaction mixture was poured into crashed ice and extracted twice with MeCl2. The combined organic phases were washed with water and brine, dried over anhydrous magnesium sulfate and evaporated. This gave 3.44 g of crude title compound as yellow solid.

Workup

  1. additionthe reaction mixture was poured
  2. extractionextracted twice with MeCl2
  3. washThe combined organic phases were washed with water and brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customevaporated

Sources & evidence

ORD record
ord-237bd909db494cb5bd79eca015fd6d74
Source dataset
uspto-grants-2006_10
Patent number
US07115611B2

Reaction notes

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