Potassium Hydroxide → HCID 58012168, compound

HRID 660896Notes

Reaction equation

HRID 660896 reaction equation
C([O:3][C:4](=[O:22])[CH2:5][N:6]1[C:10](=[O:11])[N:9]([CH2:12][CH:13]=[CH2:14])[C:8]([C:15]2[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][CH:16]=2)=[N:7]1)C.[OH-].[K+]>CO>[Cl:21][C:18]1[CH:19]=[CH:20][C:15]([C:8]2[N:9]([CH2:12][CH:13]=[CH2:14])[C:10](=[O:11])[N:6]([CH2:5][C:4]([OH:22])=[O:3])[N:7]=2)=[CH:16][CH:17]=1

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 86675482ethyl[3-(4-chlorophenyl)-4-allyl-5-oxo-4,5-dihydro-1H-1,2,4-triazol-1-yl]-acetate

Product 1

HCID 58012168HCID 58012168, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

4.88 g (15.9 mmol) of ethyl[3-(4-chlorophenyl)-4-allyl-5-oxo-4,5-dihydro-1H-1,2,4-triazol-1-yl]-acetate from Example 214A are placed in 48 ml methanol and stirred with 5 ml 20% aqueous potassium hydroxide for 2 hrs at room temperature. The solution is concentrated to ca. one half, then diluted with water and extracted with ethyl acetate. The aqueous phase is acidified with ca. 2 ml of conc. hydrochloric acid and extracted twice with 100 ml ethyl acetate each time. The last organic extracts are combined, dried over sodium sulphate, filtered and concentrated in vacuo. After drying in high vacuum, 4.20 g (90% of theory) of the target compound are thus obtained.

Workup

  1. concentrationThe solution is concentrated
  2. additiondiluted with water
  3. extractionextracted with ethyl acetate
  4. extractionextracted twice with 100 ml ethyl acetate each time
  5. dry with materialdried over sodium sulphate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customAfter drying in high vacuum, 4.20 g (90% of theory) of the target compound
  9. customare thus obtained

Sources & evidence

ORD record
ord-7f5a1a9e070e4e1f9ef3296b983f3ef5
Source dataset
uspto-grants-2011_12
Patent number
US08084481B2

Reaction notes

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