Sodium Hydroxide → HCID 178440146, compound

HRID 52971Notes

Reaction equation

HRID 52971 reaction equation
[OH:1][CH:2]([C:7]1[N:8]=[C:9]([CH2:32][CH2:33][CH3:34])[N:10]([CH2:14][C:15]2[CH:20]=[CH:19][C:18]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=3[C:27]3[NH:31][N:30]=[N:29][N:28]=3)=[CH:17][CH:16]=2)[C:11]=1[C:12]#[N:13])[C:3]([CH3:6])([CH3:5])[CH3:4].[OH-:35].[Na+]>C(O)C>[OH:1][CH:2]([C:7]1[N:8]=[C:9]([CH2:32][CH2:33][CH3:34])[N:10]([CH2:14][C:15]2[CH:20]=[CH:19][C:18]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=3[C:27]3[NH:31][N:30]=[N:29][N:28]=3)=[CH:17][CH:16]=2)[C:11]=1[C:12]([NH2:13])=[O:35])[C:3]([CH3:6])([CH3:4])[CH3:5]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 178440143HCID 178440143, compound

Product 1

HCID 178440146HCID 178440146, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 0.70 g of 4-(1-hydroxy-2,2-dimethylpropyl)-2-propyl-1-{4-[2-(tetrazol-5-yl)phenyl]phenyl}methylimidazole-5-carbonitrile [prepared as described in step (c) above] in 14 ml of 1N aqueous sodium hydroxide and 7 ml of ethanol was heated under reflux for 2 hours. At the end of this time, the ethanol in the reaction mixture was removed by evaporation under reduced pressure, and ethyl acetate and 14 ml of 1N aqueous hydrochloric acid were added to the residue. The ethyl acetate layer was separated, dried over anhydrous magnesium sulfate and concentrated by evaporation under reduced pressure, to give 0.45 g of the title compound as a powder, melting at 174°-176° C.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 2 hours
  3. customAt the end of this time, the ethanol in the reaction mixture was removed by evaporation under reduced pressure, and ethyl acetate and 14 ml of 1N aqueous hydrochloric acid
  4. additionwere added to the residue
  5. customThe ethyl acetate layer was separated
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationconcentrated by evaporation under reduced pressure

Sources & evidence

ORD record
ord-034c20a5e06447f4ab3b0f7e2c63e180
Source dataset
uspto-grants-1997_04
Patent number
US05616599

Reaction notes

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