Hydrochloric Acid → [4-(4-bromophenyl)-3-cyclopropyl-2-oxo-2,3-dihydro-1H-imidazol-1-yl]-acetic acid

HRID 660875Notes

Reaction equation

HRID 660875 reaction equation
C([O:3][C:4](=[O:22])[CH2:5][N:6]1[CH:10]=[C:9]([C:11]2[CH:16]=[CH:15][C:14]([Br:17])=[CH:13][CH:12]=2)[N:8]([CH:18]2[CH2:20][CH2:19]2)[C:7]1=[O:21])C.[OH-].[K+].Cl>CO>[Br:17][C:14]1[CH:15]=[CH:16][C:11]([C:9]2[N:8]([CH:18]3[CH2:20][CH2:19]3)[C:7](=[O:21])[N:6]([CH2:5][C:4]([OH:22])=[O:3])[CH:10]=2)=[CH:12][CH:13]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 58012242Ethyl [4-(4-bromophenyl)-3-cyclopropyl-2-oxo-2,3-dihydro-1H-imidazol-1-yl]-acetate

Product 1

HCID 58011674[4-(4-bromophenyl)-3-cyclopropyl-2-oxo-2,3-dihydro-1H-imidazol-1-yl]-acetic acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

502 mg (1.28 mmol) of ethyl[4-(4-bromophenyl)-3-cyclopropyl-2-oxo-2,3-dihydro-1H-imidazol-1-yl]-acetate from Example 124A are placed in 0.94 ml methanol, treated with 0.34 ml 20% aqueous potassium hydroxide and stirred overnight at room temperature. It is adjusted to pH 3 with 1 N hydrochloric acid, the resulting precipitate recovered by filtration, and the product washed with water and dried in vacuo. 369 mg (80% of theory) of the target compound, which is reacted without further purification, are thus obtained.

Workup

  1. filtrationthe resulting precipitate recovered by filtration
  2. washthe product washed with water
  3. customdried in vacuo
  4. custom369 mg (80% of theory) of the target compound, which is reacted without further purification
  5. customare thus obtained

Sources & evidence

ORD record
ord-99b319155a4349a5a56dc243f5c647cf
Source dataset
uspto-grants-2011_12
Patent number
US08084481B2

Reaction notes

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