Hydrochloric Acid → HCID 19862534, compound

HRID 1165139Notes

Reaction equation

HRID 1165139 reaction equation
[OH:1][C:2]1[C:16]([C:17]([CH3:20])([CH3:19])[CH3:18])=[CH:15][C:5]([C:6]([NH:8][N:9]2[CH:13]=[CH:12][N:11]=[C:10]2[CH3:14])=O)=[CH:4][C:3]=1[C:21]([CH3:24])([CH3:23])[CH3:22].Cl>O1CCCC1.C1(C)C=CC=CC=1>[OH:1][C:2]1[C:16]([C:17]([CH3:19])([CH3:18])[CH3:20])=[CH:15][C:5]([CH2:6][NH:8][N:9]2[CH:13]=[CH:12][N:11]=[C:10]2[CH3:14])=[CH:4][C:3]=1[C:21]([CH3:24])([CH3:23])[CH3:22]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 198625321-(4-Hydroxy-3,5-di-tert.-butylbenzoylamino)-2-methylimidazole

Product 1

HCID 19862534HCID 19862534, compound

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8028TetrahydrofuranSolvent

Procedure

A suspension of 200 mg of 1-(4-hydroxy-3,5-di-tert.-butylbenzoylamino)-2-methyl-1H-imidazole in 10 ml of anhydrous tetrahydrofuran is treated under an inert gas with 1.2 ml of a 2N borane-dimethyl sulfide complex solution in toluene. The mixture is then heated at reflux for 4 hours, left to cool to 0°, treated with methanolic hydrochloric acid (5 ml of methanol and 0.5 ml of conc. HCl), and again heated at reflux for 1 hour and evaporated in a vacuum. The residue is taken up in 4 ml of water and saturated sodium bicarbonate solution is added until the pH amounts to 8-9. The mixture is extracted three times with 5 ml of methylene chloride each time and, after drying, the combined methylene chloride phases are evaporated. The residue is recrystallized from cyclohexane and there is obtained 1-(4-hydroxy-3,5-di-tert.-butylbenzylamino)-2-methylimidazole of m.p. 180°.

Workup

  1. temperatureThe mixture is then heated
  2. temperatureat reflux for 4 hours
  3. waitleft
  4. temperatureto cool to 0°
  5. temperatureagain heated
  6. temperatureat reflux for 1 hour
  7. customevaporated in a vacuum
  8. additionsaturated sodium bicarbonate solution is added until the pH amounts to 8-9
  9. extractionThe mixture is extracted three times with 5 ml of methylene chloride each time
  10. customafter drying
  11. customthe combined methylene chloride phases are evaporated
  12. customThe residue is recrystallized from cyclohexane

Sources & evidence

ORD record
ord-722da50fa06d47ab89e92658214a1356
Source dataset
uspto-grants-1990_03
Patent number
US04908363

Reaction notes

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