Dimethylformamide → 2-Chloro-3-(5-methyl-4,5-dihydroisoxazol-3-yl)-4-methylsulfonylbenzoyl chloride

HRID 2167428Notes

Reaction equation

HRID 2167428 reaction equation
S(Cl)([Cl:3])=O.[Cl:5][C:6]1[C:14]([C:15]2[CH2:19][CH:18]([CH3:20])[O:17][N:16]=2)=[C:13]([S:21]([CH3:24])(=[O:23])=[O:22])[CH:12]=[CH:11][C:7]=1[C:8](O)=[O:9].CN(C)C=O>C1(C)C=CC=CC=1>[Cl:5][C:6]1[C:14]([C:15]2[CH2:19][CH:18]([CH3:20])[O:17][N:16]=2)=[C:13]([S:21]([CH3:24])(=[O:23])=[O:22])[CH:12]=[CH:11][C:7]=1[C:8]([Cl:3])=[O:9]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 24386Thionyl ChlorideHCID 221149242-Chloro-3-(5-methyl-4,5-dihydroisoxazol-3-yl)-4-methylsulfonylbenzoic acid

Product 1

HCID 221149032-Chloro-3-(5-methyl-4,5-dihydroisoxazol-3-yl)-4-methylsulfonylbenzoyl chloride

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

5.7 g (51 mmol) of thionyl chloride were added dropwise at room temperature to a solution of 13.0 g (41 mmol) of 2-chloro-3-(5-methyl-4,5-dihydroisoxazol-3-yl)-4-methylsulfonylbenzoic acid, 1 ml of dimethylformamide and 250 ml of dry toluene. The mixture was subsequently refluxed until the reaction was complete. After cooling, the solvent was distilled off. This gave 14.2 g of 2-chloro-3-(5-methyl-4,5-dihydroisoxazol-3-yl)-4-methyl-benzoyl chloride in quantitative yield.

Workup

  1. temperatureThe mixture was subsequently refluxed until the reaction
  2. temperatureAfter cooling
  3. distillationthe solvent was distilled off

Sources & evidence

ORD record
ord-3f0c99767a78448783aa1a8efe1cecdb
Source dataset
uspto-grants-2015_06
Patent number
US09045465B1

Reaction notes

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