Hydrochloric Acid → 5-(5-Chloro-2-thienyl)-4-(2-methoxyethyl)-2,4-dihydro-3H-1,2,4-triazol-3-one

HRID 574144Notes

Reaction equation

HRID 574144 reaction equation
[Cl:1][C:2]1[S:6][C:5]([C:7]([NH:9][NH:10][C:11]([NH:13][CH2:14][CH2:15][O:16][CH3:17])=[O:12])=O)=[CH:4][CH:3]=1.[OH-].[Na+].Cl>>[Cl:1][C:2]1[S:6][C:5]([C:7]2[N:13]([CH2:14][CH2:15][O:16][CH3:17])[C:11](=[O:12])[NH:10][N:9]=2)=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium Hydroxide2×HCID 595369432-[(5-Chloro-2-thienyl)carbonyl]-N-(2-methoxyethyl)hydrazinecarboxamide

Product 1

HCID 595368995-(5-Chloro-2-thienyl)-4-(2-methoxyethyl)-2,4-dihydro-3H-1,2,4-triazol-3-one

Procedure

4.85 g (17.46) mmol of the compound of Example 12A were dissolved in 17 ml (52.39 mmol) of 3M aqueous sodium hydroxide solution and heated under reflux for 168 h. After 16, 40, 64 and 88 h, in each case 1.05 g (26.19 mmol, 104.76 mmol in total) of solid sodium hydroxide were added. Using 1M hydrochloric acid, the mixture was adjusted to pH 10, and the mixture was extracted twice with in each case 30 ml of ethyl acetate. The combined organic phases were dried over sodium sulphate, filtered, freed from the solvent on a rotary evaporator and dried under high vacuum. This gave 2.44 g (54% of theory) of the title compound.

Workup

  1. temperatureheated
  2. temperatureunder reflux for 168 h
  3. extractionthe mixture was extracted twice with in each case 30 ml of ethyl acetate
  4. dry with materialThe combined organic phases were dried over sodium sulphate
  5. filtrationfiltered
  6. customfreed from the solvent on a rotary evaporator
  7. customdried under high vacuum

Sources & evidence

ORD record
ord-d7c4e70852b2458889a373c373bb2253
Source dataset
uspto-grants-2015_05
Patent number
US09034855B2

Reaction notes

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