4-Toluenesulfonyl chloride → Benzyl 3-pyridyl ketone oxime p-toluenesulfonate

HRID 365110Notes

Reaction equation

HRID 365110 reaction equation
[C:1]1([CH3:11])[CH:6]=[CH:5][C:4]([S:7](Cl)(=[O:9])=[O:8])=[CH:3][CH:2]=1.[N:12]1[CH:17]=[CH:16][CH:15]=[C:14]([C:18](=[N:26][OH:27])[CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH:13]=1>N1C=CC=CC=1>[C:1]1([CH3:11])[CH:6]=[CH:5][C:4]([S:7]([OH:27])(=[O:9])=[O:8])=[CH:3][CH:2]=1.[N:12]1[CH:17]=[CH:16][CH:15]=[C:14]([C:18](=[N:26][OH:27])[CH2:19][C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)[CH:13]=1

Participants

4

Reactant 2

HCID 73974-Toluenesulfonyl chlorideHCID 72739677Benzyl 3-pyridyl ketone oxime

Product 1

HCID 86739563Benzyl 3-pyridyl ketone oxime p-toluenesulfonate

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent2×

Procedure

A solution of 7.7 g of p-toluenesulfonyl chloride in 15 ml of pyridine is added dropwise in the course of 5 minutes to a solution, which is stirred at -10°, of 8.5 g of benzyl 3-pyridyl ketone oxime in 20 ml of pyridine. The reaction mixture is placed in a refrigerator for 24 hours and then poured onto ice/water. After some stirring and grinding, the oil which has separated out solidifies to crystals. These are filtered off with suction, washed with water and dried under a high vacuum. Benzyl 3-pyridyl ketone oxime p-toluenesulfonate is obtained and this is employed in the next stage without further purification.

Workup

  1. additionpoured onto ice/water
  2. customAfter some stirring and grinding
  3. customthe oil which has separated out solidifies to crystals
  4. filtrationThese are filtered off with suction
  5. washwashed with water
  6. customdried under a high vacuum

Sources & evidence

ORD record
ord-3ee1c9d3e809476ebf121fb416a78746
Source dataset
uspto-grants-1986_08
Patent number
US04608382

Reaction notes

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