Hydrochloric Acid → HCID 19802766, compound

HRID 1645947Notes

Reaction equation

HRID 1645947 reaction equation
[CH2:1]([C:5]1[N:9]([CH2:10][C:11]2[CH:16]=[CH:15][C:14]([O:17][CH:18]([C:25]([OH:27])=[O:26])[C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)=[CH:13][CH:12]=2)[C:8]([S:28][CH2:29][C:30]2[CH:35]=[CH:34][C:33]([Cl:36])=[CH:32][CH:31]=2)=[N:7][N:6]=1)[CH2:2][CH2:3][CH3:4].[OH:37]O.Cl>C(O)(=O)C.O.CCOC(C)=O>[CH2:1]([C:5]1[N:9]([CH2:10][C:11]2[CH:12]=[CH:13][C:14]([O:17][CH:18]([C:25]([OH:27])=[O:26])[C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)=[CH:15][CH:16]=2)[C:8]([S:28]([CH2:29][C:30]2[CH:31]=[CH:32][C:33]([Cl:36])=[CH:34][CH:35]=2)=[O:37])=[N:7][N:6]=1)[CH2:2][CH2:3][CH3:4]

Participants

8

Reactant 3

HCID 313Hydrochloric AcidHCID 784Hydrogen PeroxideHCID 9958372HCID 9958372, compound

Product 1

HCID 19802766HCID 19802766, compoundYield 51%

Reagents, catalysts & solvents 4

HCID 176Acetic AcidCatalystHCID 176Acetic AcidSolventHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a stirred solution of 60 mg (0.11 mmol) of 3-butyl-4-[[4-[1-carboxy-1-phenylmethoxy]phenyl]methyl]-5-(4-chlorobenzylthio) -4H-1,2,4-triazole from (Example 5) in 0.75 ml of glacial acetic acid was added gradually 0.75 ml of 30% hydrogen peroxide in H2O. The solution became turbid during the addition but largely clarified within a few minutes. After adding an additional 4 drops of acetic acid, the mixture was stirred at room temperature in a stoppered flask for 16 hours. It was then diluted with 50 ml of EtOAc and shaken with 50 ml of dilute HCl (pH 2.5). The aqueous phase was extracted with an additional 3 portions of EtOAc. The combined EtOAc fractions were washed once with dilute HCl (pH 2), then dried (MgSO4), filtered, and concentrated. Trituration of the residue with Et2O gave a gum. Upon decantation of the Et2O and drying in vacuo, 31 mg (51%) of the title compound was obtained as a stiff foam, mp 76°-78° C. dec.

Workup

  1. additionduring the addition
  2. waitlargely clarified within a few minutes
  3. extractionThe aqueous phase was extracted with an additional 3 portions of EtOAc
  4. washThe combined EtOAc fractions were washed once with dilute HCl (pH 2)
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customTrituration of the residue with Et2O gave a gum
  9. dry with materialUpon decantation of the Et2O and drying in vacuo

Sources & evidence

ORD record
ord-02125f41b8ec482e817d61c167d69a0d
Source dataset
uspto-grants-1993_01
Patent number
US05177095

Reaction notes

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