Hydrochloric Acid → HCID 23046249, compound

HRID 2107639Notes

Reaction equation

HRID 2107639 reaction equation
[C:1]([CH2:5][CH2:6][S:7][C:8]1[N:9]([CH2:13][C:14]2[CH:19]=[C:18]([F:20])[CH:17]=[C:16]([F:21])[CH:15]=2)[CH:10]=[CH:11][N:12]=1)([O:3]C)=[O:2].Cl>[OH-].[Na+]>[C:1]([CH2:5][CH2:6][S:7][C:8]1[N:9]([CH2:13][C:14]2[CH:19]=[C:18]([F:20])[CH:17]=[C:16]([F:21])[CH:15]=2)[CH:10]=[CH:11][N:12]=1)([OH:3])=[O:2]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 23046253HCID 23046253, compound

Product 1

HCID 23046249HCID 23046249, compound

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

2-(2-Carbomethoxyethylthio)-1-(3,5-difluorobenzyl)imidazole (3.12, 0.010 mole) is stirred with 2.5N aqueous sodium hydroxide (20 ml) and the reaction mixture is heated at reflux for one hour and then cooled and neutralized with concentrated hydrochloric acid. The mixture is then extracted three times with ether and the combine ether extracts are concentrated. A crystalline solid is obtained by trituration of the residue with boiling hexane. This is recrystallized from ethyl acetate-hexane to give 2-(2-carboxyethylthio)-1-(3,5-difluorobenzyl)imidazole.

Workup

  1. temperaturethe reaction mixture is heated
  2. temperatureat reflux for one hour
  3. extractionThe mixture is then extracted three times with ether
  4. concentrationthe combine ether extracts are concentrated
  5. customA crystalline solid is obtained by trituration of the residue with boiling hexane
  6. customThis is recrystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-0b10f0c28b814c588059da8fee0fc36e
Source dataset
uspto-grants-1990_06
Patent number
US04935438

Reaction notes

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