Hydrochloric Acid → HCID 136209504, compound

HRID 1165155Notes

Reaction equation

HRID 1165155 reaction equation
[NH2:1][N:2]1[CH:6]=[CH:5][N:4]=[C:3]1[N:7]1[CH2:12][CH2:11][O:10][CH2:9][CH2:8]1.Cl.[OH:14][C:15]1[C:22]([C:23]([CH3:26])([CH3:25])[CH3:24])=[CH:21][C:18]([CH:19]=O)=[CH:17][C:16]=1[C:27]([CH3:30])([CH3:29])[CH3:28]>C(O)C>[OH:14][C:15]1[C:22]([C:23]([CH3:25])([CH3:24])[CH3:26])=[CH:21][C:18]([CH:19]=[N:1][N:2]2[CH:6]=[CH:5][N:4]=[C:3]2[N:7]2[CH2:8][CH2:9][O:10][CH2:11][CH2:12]2)=[CH:17][C:16]=1[C:27]([CH3:30])([CH3:29])[CH3:28]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 732193,5-Di-tert-butyl-4-hydroxybenzaldehydeHCID 19862535HCID 19862535, compound

Product 1

HCID 136209504HCID 136209504, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

1.18 g of 1-amino-2-morpholinoimidazole are dissolved in 50 ml of ethanol and treated with 3.5 ml of 2N hydrochloric acid. After the addition of 1.65 g of 4-hydroxy-3,5-di-tert.-butylbenzaldehyde, the reaction mixture is stirred at room temperature overnight. The solvent is subsequently removed by evaporation in a vacuum. The residue is treated with 20 ml of water and saturated sodium carbonate solution is added up to an alkaline reaction. The separated, colorless product is removed by filtration and purified by column chromatography (eluent methylene chloride/methanol 10%). By recrystallization from water/methanol, there is obtained pure 1-(4-hydroxy-3,5-di-tert.-butylbenzylideneamino)-2-morpholinoimidazole of m.p. 185°-187°.

Workup

  1. customThe solvent is subsequently removed by evaporation in a vacuum
  2. additionThe residue is treated with 20 ml of water and saturated sodium carbonate solution
  3. additionis added up to an alkaline reaction
  4. customThe separated, colorless product is removed by filtration
  5. custompurified by column chromatography (eluent methylene chloride/methanol 10%)
  6. customBy recrystallization from water/methanol

Sources & evidence

ORD record
ord-1a761764d8484673b8c500543e22b1ab
Source dataset
uspto-grants-1990_03
Patent number
US04908363

Reaction notes

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