Potassium Hydroxide → HCID 19699324, compound

HRID 1735900Notes

Reaction equation

HRID 1735900 reaction equation
[F:1][C:2]1[CH:11]=[C:10]([F:12])[CH:9]=[C:8]2[C:3]=1[CH2:4][CH2:5][CH:6]([N:13]1[C:17]([C:18]([O:20]CC)=[O:19])=[CH:16][NH:15][C:14]1=[S:23])[CH2:7]2.[OH-].[K+]>C(O)C.O>[F:1][C:2]1[CH:11]=[C:10]([F:12])[CH:9]=[C:8]2[C:3]=1[CH2:4][CH2:5][CH:6]([N:13]1[C:17]([C:18]([OH:20])=[O:19])=[CH:16][NH:15][C:14]1=[S:23])[CH2:7]2

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 19699502HCID 19699502, compound

Product 1

HCID 19699324HCID 19699324, compoundYield 91.9%

Reagents, catalysts & solvents 1

HCID 19096565Water ethanolSolvent

Procedure

A mixture of ethyl 3-(5,7-difluoro-1,2,3,4-tetrahydronaphthalen-2-yl)-2-thioxo-2,3-dihydro-1H-imidazole-4-carboxylate (4.6 g, 13.6 mmol), prepared as in Example 24, and potassium hydroxide (3.14 g, 47.6 mmol) in 130 mL of ethanol/water (10:3) was stirred at 85°-90° C. for 5 hours. The solvent was removed by evaporation and the residue was dissolved in water. The solution was acidified with 1N hydrochloric acid to a pH of 1 giving a crystalline material. Isolation of the material by filtration gave 3-(5,7-difluoro-1,2,3,4-tetrahydronaphthalen-2-yl)-2-thioxo-2,3-dihydro-1H-imidazole-4-carboxylic acid (3.86 g, 12.5 mmol), m.p. 250°-252° C.

Workup

  1. customThe solvent was removed by evaporation
  2. dissolutionthe residue was dissolved in water
  3. customgiving a crystalline material
  4. filtrationIsolation of the material by filtration

Sources & evidence

ORD record
ord-9ad68494a4e84f7481ee81b7b5377b46
Source dataset
uspto-grants-1996_07
Patent number
US05538988

Reaction notes

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