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

HRID 322055Notes

Reaction equation

HRID 322055 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-].[OH:19][NH3+:20].C(=O)([O-])[O-].[Na+].[Na+]>CO.O>[Cl:1][C:2]1[C:11]([CH:12]=[N:20][OH:19])=[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 21645Hydroxylamine HClHCID 18517410Methyl 2-chloro-3-formyl-4-methylsulfonylbenzoate

Product 1

HCID 86584467Methyl 2-chloro-3-hydroxyiminomethyl-4-methylsulfonylbenzoateYield 96.6%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent2×

Procedure

55.23 g (0.199 mol) of methyl 2-chloro-3-formyl-4-methylsulfonylbenzoate are suspended in 400 ml of methanol/100 ml of water and treated with 15.27 g (0.219 mol) of hydroxylammonium chloride. 11.56 g (0.11 mol) of sodium carbonate—dissolved in 100 ml of water—are then slowly added dropwise at room temperature. After stirring at room temperature for 4 hours, the methanol is removed in a rotary evaporator, the residue is diluted with water and the mixture is extracted three times with dichlormethane. 56.05 g (96% of theory) of methyl 2-chloro-3 hydroximinomethyl-4-methylsulfonylbenzoate having a melting point of 126-130° C. are obtained.

Workup

  1. additionare then slowly added dropwise at room temperature
  2. customthe methanol is removed in a rotary evaporator
  3. additionthe residue is diluted with water
  4. extractionthe mixture is extracted three times with dichlormethane

Sources & evidence

ORD record
ord-0d46fc7f029142a692be586fe3a9b785
Source dataset
uspto-grants-2001_04
Patent number
US06211216B1

Reaction notes

Loading…