4-Toluenesulfonyl chloride → 4-Propionylpyridine oxime tosylate

HRID 371400Notes

Reaction equation

HRID 371400 reaction equation
[C:1](=[N:10][OH:11])([C:4]1[CH:9]=[CH:8][N:7]=[CH:6][CH:5]=1)[CH2:2][CH3:3].[C:12]1([CH3:22])[CH:17]=[CH:16][C:15]([S:18](Cl)(=[O:20])=[O:19])=[CH:14][CH:13]=1>N1C=CC=CC=1>[S:18]([C:15]1[CH:16]=[CH:17][C:12]([CH3:22])=[CH:13][CH:14]=1)([OH:11])(=[O:20])=[O:19].[C:1](=[N:10][OH:11])([C:4]1[CH:9]=[CH:8][N:7]=[CH:6][CH:5]=1)[CH2:2][CH3:3]

Participants

4

Reactant 2

HCID 73974-Toluenesulfonyl chlorideHCID 1363417421-(Pyridin-4-yl)propan-1-one oxime

Product 1

HCID 1363872634-Propionylpyridine oxime tosylate

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To the oxime 2 of Example 2 (5.0 g, 33 mmol) dissolved in pyridine (31 mL) was added p-toluenesulfonyl chloride (7.4 g, 39 mmol) and the reaction mixture stirred at room temperature for 24 hours. Pyridine hydrochloride was removed by filtration and the filtrate concentrated under reduced pressure. The solid obtained was slurried in hexanes, filtered, and air dried to give the compound 3 as a pale peach-colored solid: NMR (CDCl3) δ 1.12 (t, 3H, J=8 Hz), 2.45 (s, 3H), 2.81 (q, 2H, J=8 Hz), and 7.27-7.98 (m, 8H).

Workup

  1. customPyridine hydrochloride was removed by filtration
  2. concentrationthe filtrate concentrated under reduced pressure
  3. customThe solid obtained
  4. filtrationfiltered
  5. customair dried

Sources & evidence

ORD record
ord-f2d87eba931649f592dc6d67dec8dc33
Source dataset
uspto-grants-1985_07
Patent number
US04532250

Reaction notes

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