Hydrochloric Acid → HCID 19862531, compound

HRID 1165162Notes

Reaction equation

HRID 1165162 reaction equation
[OH:1][C:2]1[C:17]([C:18]([CH3:21])([CH3:20])[CH3:19])=[CH:16][C:5]([CH:6]=[N:7][N:8]2[CH:12]=[CH:11][N:10]=[C:9]2[CH2:13][CH2:14][CH3:15])=[CH:4][C:3]=1[C:22]([CH3:25])([CH3:24])[CH3:23].Cl.[H][H]>CO.[Pd]>[OH:1][C:2]1[C:17]([C:18]([CH3:21])([CH3:20])[CH3:19])=[CH:16][C:5]([CH2:6][NH:7][N:8]2[CH:12]=[CH:11][N:10]=[C:9]2[CH2:13][CH2:14][CH3:15])=[CH:4][C:3]=1[C:22]([CH3:23])([CH3:25])[CH3:24]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 136209527HCID 136209527, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 19862531HCID 19862531, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

9.9 g of 1-(4-hydroxy-3,5-di-tert.-butylbenzylideneamino)-2-propylimidazole are hydrogenated at normal pressure and room temperature in 200 ml of methanol and 29 ml of 1N hydrochloric acid in the presence of 1 g of a palladium catalyst (5% on carbon). After 700 ml of hydrogen have been taken up, the catalyst is removed by filtration and the filtrate is evaporated. The residue is taken up with 100 ml of water, and saturated sodium bicarbonate solution is added up to a neutral reaction (pH=7). The separated crystals are removed by filtration and taken up in 300 ml of methylene chloride. The methylene chloride solution is washed once with water, dried and evaporated. The residue is dissolved in 50 ml of hot isopropyl ether. The crystals which separate upon cooling are removed by filtration, washed with isopropyl ether and n-hexane and dried at 60° in a vacuum. There is obtained 1-(4-hydroxy-3,5-di-tert.-butylbenzylamino)-2-propylimidazole of m.p. 122°-123°.

Workup

  1. customthe catalyst is removed by filtration
  2. customthe filtrate is evaporated
  3. additionis added up to a neutral reaction (pH=7)
  4. customThe separated crystals are removed by filtration
  5. washThe methylene chloride solution is washed once with water
  6. customdried
  7. customevaporated
  8. dissolutionThe residue is dissolved in 50 ml of hot isopropyl ether
  9. customThe crystals which separate
  10. temperatureupon cooling
  11. customare removed by filtration
  12. washwashed with isopropyl ether and n-hexane
  13. customdried at 60° in a vacuum

Sources & evidence

ORD record
ord-8577b92790ec401a815f3338eb86e63c
Source dataset
uspto-grants-1990_03
Patent number
US04908363

Reaction notes

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