Triethylamine → Methanesulfonic acid 6-methyl-pyridin-3-ylmethyl ester

HRID 423141Notes

Reaction equation

HRID 423141 reaction equation
[CH3:1][C:2]1[N:7]=[CH:6][C:5]([CH2:8][OH:9])=[CH:4][CH:3]=1.C(N(CC)CC)C.[CH3:17][S:18](Cl)(=[O:20])=[O:19]>O1CCCC1>[CH3:1][C:2]1[N:7]=[CH:6][C:5]([CH2:8][O:9][S:18]([CH3:17])(=[O:20])=[O:19])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 11228788(6-Methylpyridin-3-yl)methanol

Product 1

HCID 58278804Methanesulfonic acid 6-methyl-pyridin-3-ylmethyl ester

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (6-Methyl-pyridin-3-yl)-methanol (24.36 kg, 198 mol) dissolved in tetrahydrofuran (80 kg) under nitrogen at −3° C. was added triethylamine (22.14 kg, 218.8 mol) over 30 mins followed by methanesulphonyl chloride (23.16 kg, 202.2 mol) over 3 hr and the slurry stirred for an additional 30 mins. The slurry was then filtered to remove triethylamine hydrochloride and the cake washed four times with tetraydrofuran (21.6 kg). An aliquot was removed and concentrated and analysed.

Workup

  1. filtrationThe slurry was then filtered
  2. customto remove triethylamine hydrochloride
  3. washthe cake washed four times with tetraydrofuran (21.6 kg)
  4. customAn aliquot was removed
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-8efbf6aca8164368b82e4dc1a0fd284a
Source dataset
uspto-grants-2012_01
Patent number
US08101750B2

Reaction notes

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