Hydrochloric Acid → HCID 19862550, compound

HRID 1165160Notes

Reaction equation

HRID 1165160 reaction equation
[OH:1][C:2]1[C:15]([C:16]([CH3:19])([CH3:18])[CH3:17])=[CH:14][C:5]([CH:6]=[N:7][N:8]2[CH:12]=[C:11]([CH3:13])[N:10]=[CH:9]2)=[CH:4][C:3]=1[C:20]([CH3:23])([CH3:22])[CH3:21].Cl.O.[H][H]>CO.[C].[Pd]>[OH:1][C:2]1[C:15]([C:16]([CH3:18])([CH3:17])[CH3:19])=[CH:14][C:5]([CH2:6][NH:7][N:8]2[CH:12]=[C:11]([CH3:13])[N:10]=[CH:9]2)=[CH:4][C:3]=1[C:20]([CH3:23])([CH3:22])[CH3:21]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 136199534HCID 136199534, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 19862550HCID 19862550, compound

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolvent

Procedure

6.1 g of 1-(4-hydroxy-3,5-di-tert.-butylbenzylideneamino)-4-methylimidazole are hydrogenated at normal pressure and room temperature in 100 ml of methanol, 21 ml of 1N hydrochloric acid and 30 ml of water in the presence of palladium-carbon. After 500 ml of hydrogen have been taken up, the mixture is filtered. The filtrate is evaporated to a volume of 50 ml. Then, 50 ml of water are added and the mixture is treated with saturated sodium bicarbonate solution up to a neutral reaction (pH=7). The separated crystals are removed by filtration, and taken up with methylene chloride. The methylene chloride solution is washed once with water, dried and evaporated. The residue is triturated with cold ether. Thereafter the solid is removed by filtration, washed with ether and n-hexane and dried at 60° in a vacuum. There is obtained 1-(4-hydroxy-3,5-di-tert.-butylbenzylamino)-4-methylimidazole of m.p. 150°-151°.

Workup

  1. filtrationthe mixture is filtered
  2. customThe filtrate is evaporated to a volume of 50 ml
  3. additionThen, 50 ml of water are added
  4. additionthe mixture is treated with saturated sodium bicarbonate solution up to a neutral reaction (pH=7)
  5. customThe separated crystals are removed by filtration
  6. washThe methylene chloride solution is washed once with water
  7. customdried
  8. customevaporated
  9. customThe residue is triturated with cold ether
  10. customThereafter the solid is removed by filtration
  11. washwashed with ether and n-hexane
  12. customdried at 60° in a vacuum

Sources & evidence

ORD record
ord-e938ab1951134e8a9a505a4a6c032f3e
Source dataset
uspto-grants-1990_03
Patent number
US04908363

Reaction notes

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