Sodium Hydroxide → HCID 15293908, compound

HRID 2210570Notes

Reaction equation

HRID 2210570 reaction equation
[OH-:1].[Na+].[OH:3][CH:4]([C:8]1[N:9]=[C:10]([CH2:34][CH2:35][CH3:36])[N:11]([CH2:15][C:16]2[CH:21]=[CH:20][C:19]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=3[C:28]([C:30]([O:32]C)=[O:31])=[O:29])=[CH:18][CH:17]=2)[C:12]=1[C:13]#[N:14])[CH:5]([CH3:7])[CH3:6]>C(O)C>[OH:3][CH:4]([C:8]1[N:9]=[C:10]([CH2:34][CH2:35][CH3:36])[N:11]([CH2:15][C:16]2[CH:21]=[CH:20][C:19]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=3[C:28]([C:30]([OH:32])=[O:31])=[O:29])=[CH:18][CH:17]=2)[C:12]=1[C:13]([NH2:14])=[O:1])[CH:5]([CH3:7])[CH3:6]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 19378978HCID 19378978, compound

Product 1

HCID 15293908HCID 15293908, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

4 ml of a 1N aqueous solution of sodium hydroxide were added to a solution of 170 mg of 4-(1-hydroxy-2-methylpropyl)-1-[(2'-methoxalylbiphenyl-4-yl)methyl]-2-propylimidazole-5-carbonitrile [prepared as described in step (a) above] dissolved in 3 ml of hot ethanol, and the resulting mixture was stirred under reflux for 2.5 hours. At the end of this time, the ethanol was removed by evaporation under reduced pressure, and ethyl aceate was added to the residual aqueous solution. 4 ml of 1N aqueous hydrochloric acid were added to the mixture, after which the ethyl acetate layer was separated. This extract was then dried over anhydrous magnesium sulfate, and the solvent was removed by evaporation under reduced pressure to give 140 mg of the title compound as crystals, softening at 150° C., and melting at 165°-170° C. (with decomposition).

Workup

  1. temperatureunder reflux for 2.5 hours
  2. customAt the end of this time, the ethanol was removed by evaporation under reduced pressure, and ethyl aceate
  3. additionwas added to the residual aqueous solution
  4. addition4 ml of 1N aqueous hydrochloric acid were added to the mixture
  5. customafter which the ethyl acetate layer was separated
  6. dry with materialThis extract was then dried over anhydrous magnesium sulfate
  7. customthe solvent was removed by evaporation under reduced pressure

Sources & evidence

ORD record
ord-1ad19011196e47f2975e81693907899d
Source dataset
uspto-grants-1995_10
Patent number
US05459148

Reaction notes

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