(Chlorothio)formyl chloride → Methyl 2-chloro-3-(1,3,4-oxathiazolin-2-on-5-yl)-4-methylsulfonylbenzoate

HRID 1276124Notes

Reaction equation

HRID 1276124 reaction equation
Cl[C:2]([S:4]Cl)=[O:3].[NH2:6][C:7]([C:9]1[C:10]([Cl:23])=[C:11]([CH:16]=[CH:17][C:18]=1[S:19]([CH3:22])(=[O:21])=[O:20])[C:12]([O:14][CH3:15])=[O:13])=[O:8]>C1(C)C=CC=CC=1>[Cl:23][C:10]1[C:9]([C:7]2[O:8][C:2](=[O:3])[S:4][N:6]=2)=[C:18]([S:19]([CH3:22])(=[O:20])=[O:21])[CH:17]=[CH:16][C:11]=1[C:12]([O:14][CH3:15])=[O:13]

Participants

4

Reactant 2

HCID 75990(Chlorothio)formyl chlorideHCID 22114953Methyl 3-aminocarbonyl-2-chloro-4-methylsulfonylbenzoate

Product 1

HCID 22114911Methyl 2-chloro-3-(1,3,4-oxathiazolin-2-on-5-yl)-4-methylsulfonylbenzoateYield 70.5%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

9.80 g (75 mmol) of chlorocarbonylsulfenyl chloride were added dropwise to a solution of 4.37 g (15 mmol) of methyl 3-aminocarbonyl-2-chloro-4-methylsulfonylbenzoate in 150 ml of dry toluene. The mixture was stirred under reflux for 48 hours, and the solvent was then removed under reduced pressure and the residue was chromatographed over silica gel (eluent: ethyl acetate/cyclohexane=1/1). 3.70 g (70% of theory) of methyl 2-chloro-3-(1,3,4-oxathiazolin-2-on-5-yl)-4-methylsulfonylbenzoate were obtained.

Workup

  1. temperatureunder reflux for 48 hours
  2. customthe solvent was then removed under reduced pressure
  3. customthe residue was chromatographed over silica gel (eluent: ethyl acetate/cyclohexane=1/1)

Sources & evidence

ORD record
ord-3f782baec5834626a2c3e22c868db154
Source dataset
uspto-grants-2000_12
Patent number
US06165944

Reaction notes

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