Hydrochloric Acid → HCID 15070193, compound

HRID 373365Notes

Reaction equation

HRID 373365 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][N:9]=[C:10]2[C:14](=O)[O:13][C:12]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=3[F:22])=[N:11]2)=[CH:4][C:3]=1[CH2:23][O:24][CH2:25][CH2:26][CH:27]([CH3:29])[CH3:28].O.[NH3:31].Cl>CC(C)=O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:12]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=3[F:22])=[N:11][C:10]([C:14]([NH2:31])=[O:13])=[N:9]2)=[CH:4][C:3]=1[CH2:23][O:24][CH2:25][CH2:26][CH:27]([CH3:29])[CH3:28]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 12896473Azane;hydrateHCID 178447041HCID 178447041, compound

Product 1

HCID 15070193HCID 15070193, compoundYield 82.3%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

In 10 ml of acetone, 1.294 g (3 mmol) of 4-[4-chloro-3-[(3-methylbutoxy)methyl]phenyl hydrazono]-2-(2-fluorophenyl)-2-oxazolin-5-one synthesized in the similar way to Examples 1~2, Reference Example 1 was suspended, followed by the addition of 0.6 ml of concentrated ammonia water and 30-minute stirring at room temperature. 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, and this crude product was purified by subjecting it to silica gel chromatography using hexane/ethyl acetate (1/2, v/v) as developing solvent and recrystallized from ethyl acetate-hexane to obtain 1.062 g (82.3% yield) of 1-[4-chloro-3-[(3-methylbutoxy)methyl]phenyl]-5-(2-fluorophenyl)-1H-1,2,4-triazole-3-carboxamide (m.p. 113°-115° 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
  10. customrecrystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-5327525875884187a5c8062a1f07fdf5
Source dataset
uspto-grants-1992_11
Patent number
US05162583

Reaction notes

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