Sodium Hydroxide → 4-Cyclopropyl-[1,2,3]thiadiazole-5-carboxylicacid

HRID 506439Notes

Reaction equation

HRID 506439 reaction equation
[CH:1]1([C:4]2[N:5]=[N:6][S:7][C:8]=2[C:9]([O:11]C)=[O:10])[CH2:3][CH2:2]1.[OH-].[Na+]>CO>[CH:1]1([C:4]2[N:5]=[N:6][S:7][C:8]=2[C:9]([OH:11])=[O:10])[CH2:2][CH2:3]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 57659801HCID 57659801, compound

Product 1

HCID 252473464-Cyclopropyl-[1,2,3]thiadiazole-5-carboxylicacidYield 86.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Methyl 4-cyclopropyl-1,2,3-thiadiazole-5-carboxylate (35 g; 190 mmols) was dissolved in methanol (150 ml), and an aqueous solution (150 ml) of sodium hydroxide (15 g; 360 mmols) was added dropwise thereto over 30 minutes under cooling in an ice-bath. After completion of the dropwise addition, the mixture was stirred for 2 hours at room temperature, and methanol was evaporated under reduced pressure, followed by washing with ethyl acetate. The aqueous layer was acidified by using concentrated hydrochloric acid, and was extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate, and then the solvent was evaporated under reduced pressure. The residue was washed with a mixed solvent of hexane-ethyl acetate to thereby obtain 28 g of 4-cyclopropyl-1,2,3-thiadiazole-5-carboxylic acid.

Workup

  1. temperatureover 30 minutes under cooling in an ice-bath
  2. additionAfter completion of the dropwise addition
  3. custommethanol was evaporated under reduced pressure
  4. washby washing with ethyl acetate
  5. extractionwas extracted with ethyl acetate
  6. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  7. customthe solvent was evaporated under reduced pressure
  8. washThe residue was washed with a mixed solvent of hexane-ethyl acetate

Sources & evidence

ORD record
ord-cd8153a7ef7643a4a28438ca3e5cdf72
Source dataset
uspto-grants-2010_08
Patent number
US07786040B2

Reaction notes

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