Hydrochloric Acid → HCID 135907034, compound

HRID 1947218Notes

Reaction equation

HRID 1947218 reaction equation
Cl.[CH:2]([N:5]1[C:9]([C:10]2[CH:15]=[C:14]([CH:16]([CH3:18])[CH3:17])[C:13]([O:19]COC)=[CH:12][C:11]=2[O:23]COC)=[N:8][NH:7][C:6]1=[O:27])([CH3:4])[CH3:3].C(=O)([O-])O.[Na+]>CO>[OH:23][C:11]1[CH:12]=[C:13]([OH:19])[C:14]([CH:16]([CH3:18])[CH3:17])=[CH:15][C:10]=1[C:9]1[N:5]([CH:2]([CH3:4])[CH3:3])[C:6](=[O:27])[NH:7][N:8]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 59829809HCID 59829809, compound

Product 1

HCID 135907034HCID 135907034, compoundYield 74.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

5 N hydrochloric acid (7 mL) was added to a methanol (13 mL) solution of 4-isopropyl-5-(5-isopropyl-2,4-bis-methoxymethoxyphenyl)-2,4-dihydro-[1,2,4]triazol-3-one (F63-06, 1.03 g, 2.82 mmol) and the mixture was stirred overnight. After cooling to ice cold conditions, the reaction mixture was neutralized by adding saturated aqueous sodium hydrogencarbonate. The solution was extracted with ethyl acetate, and the extract was washed with water and then with saturated sodium chloride solution. After drying the extract over anhydrous sodium, sodium sulfate was removed by filtration and the solvent was distilled off under reduced pressure to obtain white solids. After crude purification by silica gel column chromatography (chloroform, methanol), the solids were further purified by silica gel column chromatography (NHsilica, diethyl ether, methanol) to obtain 5-(2,4-dihydroxy-5-isopropylphenyl)-4-isopropyl-2,4-dihydro-[1,2,4]triazol-3-one (OH-a21, white solids, 581 mg, 74%).

Workup

  1. temperatureAfter cooling to ice cold conditions
  2. extractionThe solution was extracted with ethyl acetate
  3. washthe extract was washed with water
  4. customAfter drying the
  5. extractionextract over anhydrous sodium, sodium sulfate
  6. customwas removed by filtration
  7. distillationthe solvent was distilled off under reduced pressure
  8. customto obtain white solids
  9. customAfter crude purification by silica gel column chromatography (chloroform, methanol)
  10. customthe solids were further purified by silica gel column chromatography (NHsilica, diethyl ether, methanol)

Sources & evidence

ORD record
ord-7c171a588d5b474aa68a7b79a4d6c147
Source dataset
uspto-grants-2013_03
Patent number
US08399464B2

Reaction notes

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