4-Toluenesulfonyl chloride → HCID 54139320, compound

HRID 368982Notes

Reaction equation

HRID 368982 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:16]=[CH:17][CH:18]=1)[C:5]([C:7]1[C:8](=[O:15])[NH:9][C:10]([CH2:13][CH3:14])=[CH:11][CH:12]=1)=[O:6].C(N(CC)CC)C.[C:26]1([CH3:36])[CH:31]=[CH:30][C:29]([S:32](Cl)(=[O:34])=[O:33])=[CH:28][CH:27]=1>ClC(Cl)C.CN(C)C1C=CN=CC=1>[C:26]1([CH3:36])[CH:31]=[CH:30][C:29]([S:32]([O:15][C:8]2[C:7]([C:5](=[O:6])[C:4]3[CH:16]=[CH:17][CH:18]=[C:2]([Cl:1])[CH:3]=3)=[CH:12][CH:11]=[C:10]([CH2:13][CH3:14])[N:9]=2)(=[O:34])=[O:33])=[CH:28][CH:27]=1

Participants

6

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 23284540HCID 23284540, compound

Product 1

HCID 54139320HCID 54139320, compoundYield 91.9%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 63651,1-DichloroethaneSolvent

Procedure

3-(3-Chlorobenzoyl)-6-ethyl-2-pyridone (95.8 g, 366 mmol) was dissolved in 1,000 ml of dichloroethane, 56.4 ml (403 mmol) of triethylamine, 4.52 g (366 mmol) of 4-dimethylaminopyridine and 76.7 g (403 mmol) of p-toluenesulfonyl chloride were added thereto, followed by stirring at room temperature for 1 hour. The reaction solution was washed with water, 1 N hydrochloric acid-brine and dried over anhydrous magnesium sulfate. Magnesium sulfate was removed by filtration and then the resulting filtrate was concentrated under a reduced pressure. Thereafter, the resulting residue was recrystallized from ethyl acetate-hexane to give 139.90 g of 3-(3-chlorobenzoyl)-6-ethyl-2-pyridyl p-toluenesulfonate in the form of crystals. The yield was 91.9%.

Workup

  1. washThe reaction solution was washed with water, 1 N hydrochloric acid-brine
  2. dry with materialdried over anhydrous magnesium sulfate
  3. customMagnesium sulfate was removed by filtration
  4. concentrationthe resulting filtrate was concentrated under a reduced pressure
  5. customThereafter, the resulting residue was recrystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-a35c9432787f4e719aa8f8e61f055e62
Source dataset
uspto-grants-2000_10
Patent number
US06136810

Reaction notes

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