Sodium Hydroxide → HCID 22114933, compound

HRID 1276122Notes

Reaction equation

HRID 1276122 reaction equation
[Cl:1][C:2]1[C:11]([C:12]([NH:14][C:15]([CH3:19])([CH3:18])[CH2:16]Cl)=[O:13])=[C:10]([S:20]([CH3:23])(=[O:22])=[O:21])[CH:9]=[CH:8][C:3]=1[C:4]([O:6]C)=[O:5].[OH-].[Na+]>CO>[Cl:1][C:2]1[C:11]([C:12]2[O:13][CH2:16][C:15]([CH3:19])([CH3:18])[N:14]=2)=[C:10]([S:20]([CH3:23])(=[O:22])=[O:21])[CH:9]=[CH:8][C:3]=1[C:4]([OH:6])=[O:5]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 54043231HCID 54043231, compound

Product 1

HCID 22114933HCID 22114933, compoundYield 62.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 5.82 g (15 mmol) of methyl 2-chloro-3-(1-chloro-2,2-dimethyleth-2-ylaminocarbonyl)-4-methylsulfonylbenzoate and 0.81 g (20 mmol) of sodium hydroxide in 80 ml of methanol was stirred at room temperature for 8 hours. The solvent was distilled off and the residue was taken up in water and washed three times with ethyl acetate. The aqueous phase was acidified with hydrochloric acid and extracted three times with ethyl acetate. The organic phase was dried and the solvent was removed under reduced pressure. 3.10 g (56% of theory) of 2-chloro-3-(4,4-dimethyl-4,5-dihydrooxazol-2-yl)-4-methylsulfonylbenzoic acid were obtained.

Workup

  1. distillationThe solvent was distilled off
  2. washwashed three times with ethyl acetate
  3. extractionextracted three times with ethyl acetate
  4. customThe organic phase was dried
  5. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-aa124e66a1c746fba36a3c9eec662a9f
Source dataset
uspto-grants-2000_12
Patent number
US06165944

Reaction notes

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