HCID 135973970, compound → HCID 19862543, compound

HRID 1165142Notes

Reaction equation

HRID 1165142 reaction equation
[OH:1][C:2]1[C:14]([C:15]([CH3:18])([CH3:17])[CH3:16])=[CH:13][C:5]([CH:6]=[N:7][N:8]2[CH:12]=[CH:11][N:10]=[CH:9]2)=[CH:4][C:3]=1[C:19]([CH3:22])([CH3:21])[CH3:20].[H][H]>CO.Cl.[Pd]>[OH:1][C:2]1[C:14]([C:15]([CH3:17])([CH3:16])[CH3:18])=[CH:13][C:5]([CH2:6][NH:7][N:8]2[CH:12]=[CH:11][N:10]=[CH:9]2)=[CH:4][C:3]=1[C:19]([CH3:22])([CH3:21])[CH3:20]

Participants

6

Reactant 2

HCID 135973970HCID 135973970, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 19862543HCID 19862543, compound

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 313Hydrochloric AcidSolventHCID 887MethanolSolvent

Procedure

28.7 g of 1-(4-hydroxy-3,5-di-tert.-butylbenzylideneamino)imidazole are dissolved in 500 ml of methanol, whereupon 96 ml of 1N hydrochloric acid and 3 g of palladium/carbon are added and the mixture is hydrogenated at normal pressure and room temperature. After 2.2 l of hydrogen have been taken up, the catalyst is removed by filtration and the filtrate is evaporated. Eight hundred (800) ml of methylene chloride and 300 ml of water are added to the residue. The mixture is neutralized (pH=7) with saturated sodium bicarbonate solution while agitating. Then, the methylene chloride phase is separated and the aqueous phase is extracted twice with 100 ml of methylene chloride each time. The methylene chloride phases are combined, dried and evaporated. The residue is recrystallized from ethanol/water (3:1), and there is obtained 1-(4-hydroxy-3,5di-tert.-butylbenzylamino)imidazole of m.p. 178°-180°.

Workup

  1. additionare added
  2. customis hydrogenated at normal pressure and room temperature
  3. customthe catalyst is removed by filtration
  4. customthe filtrate is evaporated
  5. additionEight hundred (800) ml of methylene chloride and 300 ml of water are added to the residue
  6. customThen, the methylene chloride phase is separated
  7. extractionthe aqueous phase is extracted twice with 100 ml of methylene chloride each time
  8. customdried
  9. customevaporated
  10. customThe residue is recrystallized from ethanol/water (3:1)

Sources & evidence

ORD record
ord-2f8415d455a848dd976338daa54e7bf3
Source dataset
uspto-grants-1990_03
Patent number
US04908363

Reaction notes

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