4-Toluenesulfonyl chloride → Toluene-4-sulfonic acid 6-methyl-1-[1-(6-methyl-pyridin-3-yl)-ethyl]-2-oxo-1,2-dihydro-pyridin-4-yl ester

HRID 2068715Notes

Reaction equation

HRID 2068715 reaction equation
[OH:1][C:2]1[CH:7]=[C:6]([CH3:8])[N:5]([CH:9]([C:11]2[CH:12]=[N:13][C:14]([CH3:17])=[CH:15][CH:16]=2)[CH3:10])[C:4](=[O:18])[CH:3]=1.[CH3:19][C:20]1[CH:25]=[CH:24][C:23]([S:26](Cl)(=[O:28])=[O:27])=[CH:22][CH:21]=1.C(N(CC)CC)C>ClCCl>[CH3:8][C:6]1[N:5]([CH:9]([C:11]2[CH:12]=[N:13][C:14]([CH3:17])=[CH:15][CH:16]=2)[CH3:10])[C:4](=[O:18])[CH:3]=[C:2]([O:1][S:26]([C:23]2[CH:24]=[CH:25][C:20]([CH3:19])=[CH:21][CH:22]=2)(=[O:28])=[O:27])[CH:7]=1

Participants

5

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 596030954-Hydroxy-6-methyl-1-[1-(6-methyl-pyridin-3-yl)-ethyl]-1H-pyridin-2-one

Product 1

HCID 59603108Toluene-4-sulfonic acid 6-methyl-1-[1-(6-methyl-pyridin-3-yl)-ethyl]-2-oxo-1,2-dihydro-pyridin-4-yl esterYield 78.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A stirred mixture of the product from Step 1 (475 mg, 1.947 mmol) and 4-methylbenzenesulfonyl chloride (371 mg, 1.947 mmol) in anhydrous dichloromethane (16 ml) was treated with anhydrous triethylamine (0.81 ml, 5.839 ml) and stirring was continued at ambient temperature for 18 h. The reaction mixture was diluted with dichloromethane (150 ml), washed with water (100 ml) followed by brine (100 ml) and dried (MgSO4). The solvent was removed in vacuo and the residue purified by flash silica chromatography eluting with ethyl acetate to give toluene-4-sulfonic acid 6-methyl-1-[1-(6-methyl-pyridin-3-yl)-ethyl]-2-oxo-1,2-dihydro-pyridin-4-yl ester (609 mg) as a colourless gum which solidified on standing. LC-MS m/z 399 [M+H]+ Rt=2.10 min.

Workup

  1. washwashed with water (100 ml)
  2. dry with materialdried (MgSO4)
  3. customThe solvent was removed in vacuo
  4. customthe residue purified by flash silica chromatography
  5. washeluting with ethyl acetate

Sources & evidence

ORD record
ord-f112be3447c4419f98e404994275eff2
Source dataset
uspto-grants-2012_10
Patent number
US08299065B2

Reaction notes

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