Hydrochloric Acid → 1-(4-Hydroxy-3,5-di-tert.-butylbenzoylamino)-2-methylimidazole

HRID 1165138Notes

Reaction equation

HRID 1165138 reaction equation
Cl.[NH2:2][N:3]1[CH:7]=[CH:6][N:5]=[C:4]1[CH3:8].[OH:9][C:10]1[C:18]([C:19]([CH3:22])([CH3:21])[CH3:20])=[CH:17][C:13]([C:14](Cl)=[O:15])=[CH:12][C:11]=1[C:23]([CH3:26])([CH3:25])[CH3:24].Cl>O>[OH:9][C:10]1[C:11]([C:23]([CH3:25])([CH3:24])[CH3:26])=[CH:12][C:13]([C:14]([NH:2][N:3]2[CH:7]=[CH:6][N:5]=[C:4]2[CH3:8])=[O:15])=[CH:17][C:18]=1[C:19]([CH3:22])([CH3:21])[CH3:20]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 37871873,5-Di-tert-butyl-4-hydroxybenzoyl chlorideHCID 22167428HCID 22167428, compound

Product 1

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

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

1.0 g of 1-amino-2-methylimidazole hydrochloride and 2.0 g of 4-hydroxy-3,5-di-tert.-butylbenzoyl chloride are mixed and heated on an oil-bath for 40 minutes to 200°-210° (bath temperature), whereby the flask content melts with the evolution of HCl and then again becomes solid. The cooled flask content is dissolved in 30 ml of water, whereupon the solution is filtered and the filtrate is adjusted to pH 9 with 10% sodium carbonate solution. The separated precipitate is removed by filtration and dissolved in 25 ml of hot ethanol, whereupon the still hot solution is treated with 10 ml of water. After cooling, the separated solid is removed by filtration and recrystallized from ethyl acetate. There is obtained 1-(4-hydroxy-3,5-di-tert.-butylbenzoylamino)-2-methylimidazole of m.p. 322°-324° (dec.).

Workup

  1. temperatureheated on an oil-bath for 40 minutes to 200°-210° (bath temperature), whereby the flask content
  2. filtrationis filtered
  3. customThe separated precipitate is removed by filtration
  4. dissolutiondissolved in 25 ml of hot ethanol, whereupon the still hot solution
  5. additionis treated with 10 ml of water
  6. temperatureAfter cooling
  7. customthe separated solid is removed by filtration
  8. customrecrystallized from ethyl acetate

Sources & evidence

ORD record
ord-adca8df6e9a64c83a6392a78506ddc84
Source dataset
uspto-grants-1990_03
Patent number
US04908363

Reaction notes

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