Hydrochloric Acid → HCID 19862561, compound

HRID 1165151Notes

Reaction equation

HRID 1165151 reaction equation
[CH:1]([N:3]([N:20]1[CH:24]=[CH:23][N:22]=[CH:21]1)[CH2:4][C:5]1[CH:10]=[C:9]([C:11]([CH3:14])([CH3:13])[CH3:12])[C:8]([OH:15])=[C:7]([C:16]([CH3:19])([CH3:18])[CH3:17])[CH:6]=1)=O.CSC.B.Cl>O1CCCC1.C1(C)C=CC=CC=1.CO>[OH:15][C:8]1[C:9]([C:11]([CH3:13])([CH3:12])[CH3:14])=[CH:10][C:5]([CH2:4][N:3]([N:20]2[CH:24]=[CH:23][N:22]=[CH:21]2)[CH3:1])=[CH:6][C:7]=1[C:16]([CH3:19])([CH3:18])[CH3:17]

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 12423031(Dimethyl sulfide)trihydroboronHCID 19862555HCID 19862555, compound

Product 1

HCID 19862561HCID 19862561, compound

Reagents, catalysts & solvents 3

HCID 887MethanolSolvent2×HCID 1140TolueneSolventHCID 8028TetrahydrofuranSolvent

Procedure

3.30 g of 1-[N-formyl-N-(4-hydroxy-3,5-di-tert.-butylbenzyl)amino]imidazole are dissolved in 100 ml of absolute tetrahydrofuran. Into this solution there are injected at room temperature 20 ml of a 2 molar solution of borane-dimethyl sulfide complex [BH3.S(CH3)2 ] in toluene. The reaction mixture is subsequently heated to gentle reflux for 2 hours, cooled to 0°, treated with 20 ml of absolute methanol and heated for an additional 30 minutes. The solvent is removed completely by evaporation under reduced pressure on a rotary evaporator. The residual crystalline solid is triturated with n-hexane, removed by filtration and vacuum-dried for a short period. Thereupon, the solid obtained is suspended in 50 ml of absolute methanol and hydrogen chloride is introduced carefully while stirring up to saturation, whereby a clear solution results with strong warming. This solution is heated to gentle reflux for 1 hour and then evaporated under reduced pressure on a rotary evaporator. The residue is treated with 25 ml of ice-cold water, whereupon saturated sodium bicarbonate solution is added to a weakly alkaline reaction and the mixture is extracted three times with 25 ml of methylene chloride each time. The combined methylene chloride extracts are washed once with a small amount of water and subsequently with saturated sodium chloride solution, dried over anhydrous magnesium sulfate, filtered and evaporated. The residue is recrystallized from ethyl acetate/n-hexane and there is obtained 1-[N-(4-hydroxy-3,5-di-tert.-butylbenzyl)-N-methylamino]imidazole of m.p. 139°.

Workup

  1. customare injected at room temperature
  2. temperatureThe reaction mixture is subsequently heated
  3. temperatureto gentle reflux for 2 hours
  4. temperaturecooled to 0°
  5. temperatureheated for an additional 30 minutes
  6. customThe solvent is removed completely by evaporation under reduced pressure on a rotary evaporator
  7. customThe residual crystalline solid is triturated with n-hexane
  8. customremoved by filtration
  9. customvacuum-dried for a short period
  10. customThereupon, the solid obtained
  11. customresults with strong warming
  12. temperatureThis solution is heated
  13. temperatureto gentle reflux for 1 hour
  14. customevaporated under reduced pressure on a rotary evaporator
  15. additionThe residue is treated with 25 ml of ice-cold water, whereupon saturated sodium bicarbonate solution
  16. additionis added to a weakly alkaline reaction
  17. extractionthe mixture is extracted three times with 25 ml of methylene chloride each time
  18. washThe combined methylene chloride extracts are washed once with a small amount of water and subsequently with saturated sodium chloride solution
  19. dry with materialdried over anhydrous magnesium sulfate
  20. filtrationfiltered
  21. customevaporated
  22. customThe residue is recrystallized from ethyl acetate/n-hexane

Sources & evidence

ORD record
ord-6ba5d6da34ba440e80c55fb56b5f61cd
Source dataset
uspto-grants-1990_03
Patent number
US04908363

Reaction notes

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