4-Toluenesulfonyl chloride → HCID 86753437, compound

HRID 1457756Notes

Reaction equation

HRID 1457756 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.[CH3:12][C:13]1([CH3:27])[CH2:22][C:21](=[N:23][OH:24])[C:20]2[C:15](=[CH:16][C:17]([O:25][CH3:26])=[CH:18][CH:19]=2)[O:14]1>N1C=CC=CC=1>[S:7]([C:4]1[CH:5]=[CH:6][C:1]([CH3:11])=[CH:2][CH:3]=1)([OH:14])(=[O:9])=[O:8].[CH3:12][C:13]1([CH3:27])[CH2:22][C:21](=[N:23][OH:24])[C:20]2[C:15](=[CH:16][C:17]([O:25][CH3:26])=[CH:18][CH:19]=2)[O:14]1

Participants

4

Reactant 2

HCID 73974-Toluenesulfonyl chlorideHCID 85758659HCID 85758659, compound

Product 1

HCID 86753437HCID 86753437, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

85.8 g (0.45 mol) of p-toluenesulfonyl chloride were introduced into a solution of 88.5 g (0.4 mol) of 2,2-dimethyl-7-methoxy-4-chromanone oxime (Heterocycles 38 (1994), 305-318) in 550 ml of pyridine at 0° C. The mixture was allowed to come to room temperature and was subsequently stirred for several hours, stirred into ice/water and extracted with methylene chloride. The organic solution was washed twice with 2N hydrochloric acid and then several times with water, dried and evaporated, and the residue was recrystallized from ethanol. The 2,2-dimethyl-7-methoxy-4-chromanone oxime tosylate had a melting point of 113° C.

Workup

  1. customto come to room temperature
  2. extractionextracted with methylene chloride
  3. washThe organic solution was washed twice with 2N hydrochloric acid
  4. dry with materialseveral times with water, dried
  5. customevaporated
  6. customthe residue was recrystallized from ethanol

Sources & evidence

ORD record
ord-ee8bd7faba864982af8091198fea9375
Source dataset
uspto-grants-1998_12
Patent number
US05849755

Reaction notes

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