Sodium Carbonate → Methyl 2-chloro-3-hydroxyiminomethyl-4-methylsulfonylbenzoate

HRID 1276111Notes

Reaction equation

HRID 1276111 reaction equation
[Cl:1][C:2]1[C:11]([CH:12]=O)=[C:10]([S:14]([CH3:17])(=[O:16])=[O:15])[CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].Cl.[NH2:19][OH:20].C(=O)([O-])[O-].[Na+].[Na+]>CO.O>[Cl:1][C:2]1[C:11]([CH:12]=[N:19][OH:20])=[C:10]([S:14]([CH3:17])(=[O:16])=[O:15])[CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5]

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 443297Hydroxyamine hydrochlorideHCID 18517410Methyl 2-chloro-3-formyl-4-methylsulfonylbenzoate

Product 1

HCID 86584467Methyl 2-chloro-3-hydroxyiminomethyl-4-methylsulfonylbenzoateYield 91.4%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

15.00 g (54 mmol) of methyl 2-chloro-3-formyl-4-methylsulfonylbenzoate and 4.20 g (60 mmol) of hydroxylamine hydrochloride were taken up in 300 ml of methanol, and a solution of 3.18 g (30 mmol) of sodium carbonate in 80 ml of water was added dropwise. After the mixture had been stirred at room temperature for 12 hours, the methanol was distilled off and the residue was diluted with water and extracted with diethyl ether. The organic phase was dried and the solvent was removed. 14.40 g (91% of theory) of methyl 2-chloro-3-hydroxyiminomethyl-4-methylsulfonylbenzoate were obtained.

Workup

  1. distillationthe methanol was distilled off
  2. additionthe residue was diluted with water
  3. extractionextracted with diethyl ether
  4. customThe organic phase was dried
  5. customthe solvent was removed

Sources & evidence

ORD record
ord-780dc9d11f9c4703be3790f505727c7c
Source dataset
uspto-grants-2000_12
Patent number
US06165944

Reaction notes

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