Sodium Hydroxide → HCID 19765264, compound

HRID 1090017Notes

Reaction equation

HRID 1090017 reaction equation
[OH-].[Na+].[CH2:3]([C:5]1[C:9]([C:10]([O:12][CH3:13])=[O:11])=[C:8]([C:14]([O:16]C)=[O:15])[S:7][N:6]=1)[CH3:4]>O.CO>[CH2:3]([C:5]1[C:9]([C:10]([O:12][CH3:13])=[O:11])=[C:8]([C:14]([OH:16])=[O:15])[S:7][N:6]=1)[CH3:4]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 19765263HCID 19765263, compound

Product 1

HCID 19765264HCID 19765264, compoundYield 95.2%

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 962WaterSolvent

Procedure

A solution of 14.9 g of NaOH in 120 ml of water and 150 ml of methanol is added dropwise to 85.5 g of dimethyl 3-ethylisothiazole-4,5-dicarboxylate in 300 ml of methanol, while cooling with ice. After 2 hours, the mixture is evaporated down, 1.5 l of water are added to the residue and the mixture is stirred, and extracted with ether. The aqueous phase is acidified with concentrated hydrochloric acid and extracted by shaking with dichloromethane. The organic phases are evaporated down to give 76.4 g of 3-ethyl-4-methoxycarbonylisothiazole-5-carboxylic acid of melting point 43°-45° C.

Workup

  1. temperaturewhile cooling with ice
  2. customthe mixture is evaporated down
  3. addition1.5 l of water are added to the residue
  4. extractionextracted with ether
  5. extractionextracted
  6. stirringby shaking with dichloromethane
  7. customThe organic phases are evaporated down

Sources & evidence

ORD record
ord-45fb3d58e6e445289b75b9251c47b601
Source dataset
uspto-grants-1992_01
Patent number
US05080708

Reaction notes

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