Potassium Carbonate → 2-Chloro-3-ethoxyiminomethyl-4-methylsulfonylbenzoic acid

HRID 377542Notes

Reaction equation

HRID 377542 reaction equation
Cl.[CH2:2]([O:4][NH2:5])[CH3:3].C(=O)([O-])[O-].[K+].[K+].[Cl:12][C:13]1[C:21]([CH:22]=O)=[C:20]([S:24]([CH3:27])(=[O:26])=[O:25])[CH:19]=[CH:18][C:14]=1[C:15]([OH:17])=[O:16]>CO>[Cl:12][C:13]1[C:21]([CH:22]=[N:5][O:4][CH2:2][CH3:3])=[C:20]([S:24]([CH3:27])(=[O:26])=[O:25])[CH:19]=[CH:18][C:14]=1[C:15]([OH:17])=[O:16]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 76850O-ethylhydroxylamine hydrochlorideHCID 185174222-Chloro-3-formyl-4-methylsulfonylbenzoic acid

Product 1

HCID 541651472-Chloro-3-ethoxyiminomethyl-4-methylsulfonylbenzoic acidYield 78.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

1.63 g (0.017 mol) of ethoxyamine hydrochloride and 1.15 g (0.0085 mol) of finely pulverulent potassium carbonate were stirred for 1 hour in 60 ml of dry methanol. 4.00 g (0.015 mol) of 2-chloro-3-formyl-4-methylsulfonylbenzoic acid in 40 ml of methanol were subsequently added. After the mixture was stirred for 12 hours at room temperature, the solvent was removed, the residue was taken up in ethyl acetate, and the organic phase was washed four times with water. After the mixture had been dried and the solvent distilled off, 3.60 g of 2-chloro-3-ethoxyiminomethyl-4-methylsulfonylbenzoic acid were obtained (78% yield).

Workup

  1. customthe solvent was removed
  2. washthe organic phase was washed four times with water
  3. customAfter the mixture had been dried
  4. distillationthe solvent distilled off

Sources & evidence

ORD record
ord-9f7eb24ff1604ecdaf20b4b7d5c12209
Source dataset
uspto-grants-2000_02
Patent number
US06028035

Reaction notes

Loading…