Hydrochloric Acid → HCID 15070173, compound

HRID 373364Notes

Reaction equation

HRID 373364 reaction equation
[CH2:1]([O:5][CH2:6][C:7]1[CH:8]=[C:9]([NH:14][N:15]=[C:16]2[C:20](=O)[O:19][C:18]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)=[N:17]2)[CH:10]=[CH:11][C:12]=1[Cl:13])[CH2:2][CH2:3][CH3:4].O.[NH3:29].Cl>CC(C)=O>[CH2:1]([O:5][CH2:6][C:7]1[CH:8]=[C:9]([N:14]2[C:18]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)=[N:17][C:16]([C:20]([NH2:29])=[O:19])=[N:15]2)[CH:10]=[CH:11][C:12]=1[Cl:13])[CH2:2][CH2:3][CH3:4]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 12896473Azane;hydrateHCID 178450415HCID 178450415, compound

Product 1

HCID 15070173HCID 15070173, compoundYield 94.2%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

In 10 ml of acetone, 1.157 g (3 mmol) of 4-[(3-butoxymethyl-4-chlorophenyl)hydrazono]-2-phenyl-2-oxazolin-5-one synthesized in the similar way to Examples 1~2, Reference Example 1 was suspended, the suspension being then added with 0.6 ml of concentrated ammonia water and stirred at room temperature for 30 minutes. The resulting solution was made acid by adding 0.6 ml of concentrated hydrochloric acid and further stirred at 50° C. for 30 minutes. Acetone was distilled off and the residue was extracted by adding benzene and water. The organic layer was washed with a saturated sodium chloride aqueous solution and dried over anhydrous sodium sulfate. The solvents were distilled off to obtain a crude product. This crude product was purified by silica gel chromatography using hexane/ethyl acetate (1/2, v/v) as developing solvent and further recrystallized to obtain 1.087 g (94.2% yield) of 1-(3-butoxymethyl-4-chlorophenyl)-5-phenyl-1H-1,2,4-triazole-3-carboxamide (m.p 96°-98° C.).

Workup

  1. stirringfurther stirred at 50° C. for 30 minutes
  2. distillationAcetone was distilled off
  3. extractionthe residue was extracted
  4. additionby adding benzene and water
  5. washThe organic layer was washed with a saturated sodium chloride aqueous solution
  6. dry with materialdried over anhydrous sodium sulfate
  7. distillationThe solvents were distilled off
  8. customto obtain a crude product
  9. customThis crude product was purified by silica gel chromatography
  10. customfurther recrystallized

Sources & evidence

ORD record
ord-a5795172febe45b888ef62be81dd3fb1
Source dataset
uspto-grants-1992_11
Patent number
US05162583

Reaction notes

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