Potassium Hydroxide → [3-(5-Chloro-2-thienyl)-4-(2-methoxyethyl)-5-oxo-4,5-dihydro-1H-1,2,4-triazol-1-yl]acetic acid

HRID 574146Notes

Reaction equation

HRID 574146 reaction equation
C([O:3][C:4](=[O:22])[CH2:5][N:6]1[C:10](=[O:11])[N:9]([CH2:12][CH2:13][O:14][CH3:15])[C:8]([C:16]2[S:17][C:18]([Cl:21])=[CH:19][CH:20]=2)=[N:7]1)C.[OH-].[K+]>CO>[Cl:21][C:18]1[S:17][C:16]([C:8]2[N:9]([CH2:12][CH2:13][O:14][CH3:15])[C:10](=[O:11])[N:6]([CH2:5][C:4]([OH:22])=[O:3])[N:7]=2)=[CH:20][CH:19]=1

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 59536780Ethyl [3-(5-chloro-2-thienyl)-4-(2-methoxyethyl)-5-oxo-4,5-dihydro-1H-1,2,4-triazol-1-yl]acetate

Product 1

HCID 59536891[3-(5-Chloro-2-thienyl)-4-(2-methoxyethyl)-5-oxo-4,5-dihydro-1H-1,2,4-triazol-1-yl]acetic acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

3.2 g (9.25 mmol) of the compound of Example 14A were dissolved in 28 ml of methanol. 2.82 ml of 20% strength aqueous potassium hydroxide solution were then added. The mixture was stirred at RT for 2 h. On a rotary evaporator, the proportion of methanol was reduced by half. The mixture was then diluted with water and extracted once with 15 ml of ethyl acetate. The aqueous phase was acidified with 920 μl of concentrated hydrochloric acid and extracted twice with in each case 15 ml of ethyl acetate. The combined organic phases were dried over sodium sulphate, filtered and concentrated on a rotary evaporator. Drying under high vacuum gave 2.34 g (80% of theory) of the title compound.

Workup

  1. customOn a rotary evaporator
  2. additionThe mixture was then diluted with water
  3. extractionextracted once with 15 ml of ethyl acetate
  4. extractionextracted twice with in each case 15 ml of ethyl acetate
  5. dry with materialThe combined organic phases were dried over sodium sulphate
  6. filtrationfiltered
  7. concentrationconcentrated on a rotary evaporator
  8. customDrying under high vacuum

Sources & evidence

ORD record
ord-14d1d7415fc84591b5bfed98a2de85f6
Source dataset
uspto-grants-2015_05
Patent number
US09034855B2

Reaction notes

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