Sodium Hydroxide → HCID 67833704, compound

HRID 330005Notes

Reaction equation

HRID 330005 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[CH:9]([S:16][C:17]1[CH:26]=[CH:25][C:20]([C:21]([O:23]C)=[O:22])=[CH:19][CH:18]=1)[CH2:10][N:11]1[CH:15]=[CH:14][N:13]=[CH:12]1.[OH-].[Na+]>CO>[ClH:1].[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[CH:9]([S:16][C:17]1[CH:18]=[CH:19][C:20]([C:21]([OH:23])=[O:22])=[CH:25][CH:26]=1)[CH2:10][N:11]1[CH:15]=[CH:14][N:13]=[CH:12]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 13913551HCID 13913551, compound

Product 1

HCID 67833704HCID 67833704, compoundYield 118.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

306 mg of methyl 4-[1-(2,4-dichlorophenyl)-2-(imidazol-1-yl)ethylthio]benzoate (prepared as described in Example 3) were dissolved in 4 ml of methanol. 3 ml of a 1N aqueous solution of sodium hydroxide was added to the resulting solution, and the mixture was stirred at room temperature for 5 hours, and was then heated under reflux for 1 hour. The solvent was removed by distillation, and 1.5 ml of a 1N aqueous solution of sodium hydroxide was added to the residue. The resulting mixture was extracted with chloroform, and the aqueous layer was acidified (pH value 2 to 3) with 6N aqueous hydrochloric acid. The crystals which precipitated were collected by filtration, washed with water and dried, followed by recrystallization from a mixture of ethanol and ethyl acetate, to give 191 mg of the title compound as colorless crystals, melting at 187°-190° C.

Workup

  1. temperaturewas then heated
  2. temperatureunder reflux for 1 hour
  3. customThe solvent was removed by distillation, and 1.5 ml of a 1N aqueous solution of sodium hydroxide
  4. additionwas added to the residue
  5. extractionThe resulting mixture was extracted with chloroform
  6. customThe crystals which precipitated
  7. filtrationwere collected by filtration
  8. washwashed with water
  9. customdried
  10. customfollowed by recrystallization from a mixture of ethanol and ethyl acetate

Sources & evidence

ORD record
ord-daa357fcad3f401091000ffe329a05f5
Source dataset
uspto-grants-1990_01
Patent number
US04894385

Reaction notes

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