Ammonia → HCID 13754320, compound

HRID 980362Notes

Reaction equation

HRID 980362 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([C:16](=O)[C:17](=O)[CH3:18])[CH:8]=[C:9]([C:12]([CH3:15])([CH3:14])[CH3:13])[C:10]=1[OH:11])([CH3:4])([CH3:3])[CH3:2].[CH:21](=O)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.C([O-])(=O)C.[NH4+:33].[NH3:34]>C(O)(=O)C.O>[C:1]([C:5]1[CH:6]=[C:7]([C:16]2[N:33]=[C:21]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[NH:34][C:17]=2[CH3:18])[CH:8]=[C:9]([C:12]([CH3:15])([CH3:14])[CH3:13])[C:10]=1[OH:11])([CH3:4])([CH3:3])[CH3:2]

Participants

7

Reactant 4

HCID 222AmmoniaHCID 240BenzaldehydeHCID 517165Ammonium AcetateHCID 13568862HCID 13568862, compound

Product 1

HCID 13754320HCID 13754320, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

In 10ml of acetic acid was dissolved 0.6 g of 1-(3,5-di-tert-butyl-4-hydroxyphenyl)-1,2-propanedione and then after adding thereto 0.3 g of benzaldehyde and 2.2 g of ammonium acetate, the mixture was refluxed for 3 hours. The reaction mixture was concentrated and the residue formed was mixed with 20 ml of water, neutralized by the addition of concentration aqueous ammonia, and extracted with chloroform. The extract was dried and concentrated under reduced pressure. The crystals thus formed were purified by silica gel column chromatography using chloroform as the eluent and recrystallized from aqueous ethanol to provide 0.3 g of 4-(3,5-di-tert-butyl-4-hydroxyphenyl)-5-methyl-2-phenylimidazole.

Workup

  1. additionafter adding
  2. concentrationThe reaction mixture was concentrated
  3. customthe residue formed
  4. extractionextracted with chloroform
  5. customThe extract was dried
  6. concentrationconcentrated under reduced pressure
  7. customThe crystals thus formed
  8. customwere purified by silica gel column chromatography
  9. customrecrystallized from aqueous ethanol

Sources & evidence

ORD record
ord-78fc5f78cb584a4e89791769e277e443
Source dataset
uspto-grants-1987_01
Patent number
US04636516

Reaction notes

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