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

HRID 2167433Notes

Reaction equation

HRID 2167433 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-methylsulfonylbenzoate

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. After the mixture had been stirred for 48 hours under reflux, the solvent was removed in vacuo and the residue was chromatographed on silica gel (eluent: ethyl acetate/cyclohexane=1/1). This gave 3.70 g (70% of theory) of methyl 2-chloro-3-(1,3,4-oxathiazolin-2-on-5-yl)-4-methylsulfonylbenzoate.

Workup

  1. temperatureunder reflux
  2. customthe solvent was removed in vacuo
  3. customthe residue was chromatographed on silica gel (eluent: ethyl acetate/cyclohexane=1/1)

Sources & evidence

ORD record
ord-eb2d938f3d7f4629b72988ad9b4ed62b
Source dataset
uspto-grants-2015_06
Patent number
US09045465B1

Reaction notes

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