Acetic Acid → HCID 178433874, compound

HRID 59619

Reaction equation

HRID 59619 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([N:9]2[C:13](=[O:14])[C:12](=[N:15][NH:16][C:17]3[CH:22]=[CH:21][CH:20]=[C:19]([Br:23])[C:18]=3[O:24]C)[C:11]([CH3:26])=[N:10]2)[CH:5]=[CH:6][C:7]=1[CH3:8].C(O)(=O)C.O.C(=O)(O)[O-].[Na+]>Br>[CH3:1][C:2]1[CH:3]=[C:4]([N:9]2[C:13](=[O:14])[C:12](=[N:15][NH:16][C:17]3[CH:22]=[CH:21][CH:20]=[C:19]([Br:23])[C:18]=3[OH:24])[C:11]([CH3:26])=[N:10]2)[CH:5]=[CH:6][C:7]=1[CH3:8]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 962WaterHCID 516892Sodium BicarbonateHCID 1784863784-[(3-bromo-2-methoxyphenyl)hydrazinylidene]-2-(3,4-dimethylphenyl)-5-methylpyrazol-3-one

Product 1

HCID 178433874HCID 178433874, compound

Reagents, catalysts & solvents 1

HCID 260Hydrogen BromideSolvent

Procedure

A solution of 1-(3,4-dimethylphenyl)-3-methyl-4-(3-bromo-2-methoxyphenyl)hydrazono-5-pyrazolone(5 g) prepared as in Example 2, in 48% aqueous hydrobromic acid (200 mL) and glacial acetic acid (50 mL) was stirred and heated under reflux for about 80 hours. The reaction mixture was concentrated under vacuum to obtain a thick residue. Water (40 mL) was added and basified to pH 7-8 using saturated solution of sodium bicarbonate (20 mL). The mixture was filtered to give an orange solid, which was washed with water (25 mL) and dried in an oven at about 55° C. to about 60° C. for about 12 hours. Yield: 3.5 g

Workup

  1. temperatureheated
  2. temperatureunder reflux for about 80 hours
  3. concentrationThe reaction mixture was concentrated under vacuum
  4. customto obtain a thick residue
  5. filtrationThe mixture was filtered
  6. customto give an orange solid, which
  7. washwas washed with water (25 mL)
  8. customdried in an oven at about 55° C. to about 60° C. for about 12 hours

Sources & evidence

ORD record
ord-192beb1209844b92a742a2d9f4b045d0
Source dataset
uspto-grants-2016_09
Patent number
US09440927B2

Linked notes

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