Hydrochloric Acid → HCID 53760924, compound

HRID 2257960Notes

Reaction equation

HRID 2257960 reaction equation
[CH3:1][O:2][C:3]1[C:10]([O:11][CH3:12])=[CH:9][CH:8]=[CH:7][C:4]=1[CH:5]=O.[C:13]1([C:19]([C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[N:20]2[CH:24]=[C:23]([C:25](=[O:27])[CH3:26])[N:22]=[CH:21]2)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.[OH-].[Na+].Cl>C(O)C>[CH3:1][O:2][C:3]1[C:10]([O:11][CH3:12])=[CH:9][CH:8]=[CH:7][C:4]=1[CH:5]=[CH:26][C:25]([C:23]1[N:22]=[CH:21][N:20]([C:19]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)([C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=2)[C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)[CH:24]=1)=[O:27]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 665812,3-DimethoxybenzaldehydeHCID 104280901-(1-trityl-1H-imidazol-4-yl)ethanone

Product 1

HCID 53760924HCID 53760924, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

0.149 mole of 2,3-dimethoxybenzaldehyde is added over 5 hours at room temperature to a solution of 0.149 mole of 1-(1-triphenylmethyl-1H-imidazol-4-yl)-1-ethanone prepared in Example 2.1 in a mixture of 800 ml of ethanol and 186 ml of a 2N aqueous solution of sodium hydroxide. The reaction medium is then brought to pH 7.5 by addition of a 5N aqueous solution of hydrochloric acid. The ethanol is distilled off and a solid is formed, which precipitates. This solid is filtered off and washed with water before drying. The solid is redissolved in 2 liters of boiling 2-propanol and the insoluble salts are filtered off. Half the 2-propanol is evaporated off and the 3-(2,3-dimethoxyphenyl)-1-(1-triphenylmethyl-1H-imidazol-4-yl)-2-propen-1-one is recrystallized.

Workup

  1. distillationThe ethanol is distilled off
  2. customa solid is formed
  3. customwhich precipitates
  4. filtrationThis solid is filtered off
  5. washwashed with water
  6. custombefore drying
  7. dissolutionThe solid is redissolved in 2 liters of boiling 2-propanol
  8. filtrationthe insoluble salts are filtered off
  9. customHalf the 2-propanol is evaporated off
  10. customthe 3-(2,3-dimethoxyphenyl)-1-(1-triphenylmethyl-1H-imidazol-4-yl)-2-propen-1-one is recrystallized

Sources & evidence

ORD record
ord-3857d5a82c3d43689304ba88685fbac3
Source dataset
uspto-grants-1997_08
Patent number
US05658938

Reaction notes

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