Hydrochloric Acid → HCID 178520527, compound

HRID 1935728Notes

Reaction equation

HRID 1935728 reaction equation
[C:1]([C:4]1[C:12]2[NH:11][C:10]([CH2:13][CH2:14][C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)=[N:9][C:8]=2[CH:7]=[CH:6][CH:5]=1)(=[O:3])[CH3:2].[OH-].[Na+].Cl>C(O)C>[NH:9]1[CH:8]=[CH:12][N:11]=[C:10]1[CH:13]=[CH:2][C:1]([C:4]1[C:12]2[NH:11][C:10]([CH2:13][CH2:14][C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)=[N:9][C:8]=2[CH:7]=[CH:6][CH:5]=1)=[O:3]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 178466129HCID 178466129, compound

Product 1

HCID 178520527HCID 178520527, compoundYield 54%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Ethanol (15 mL) was added to 4-acetyl-2-(2-phenylethyl)benzimidazole (1 g) obtained in Reference Example 1 and 2-imidazolecarboxyaldehyde (304 mg) . Sodium hydroxide (405 mg) was added to the mixture and the mixture was stirred overnight at room temperature. The reaction solution was poured into ice water, adjusted to pH 8 with 4 N hydrochloric acid and then extracted with ethyl acetate. The organic layer was washed with water and brine in that order and then dried over anhydrous sodium sulfate. After evaporation of the solvent under a reduced pressure, the resulting residue was purified by a silica gel column chromatography (eluent: hexane/ethyl acetate) to obtain the title compound (0.35 g).

Workup

  1. customobtained in Reference Example 1 and 2-imidazolecarboxyaldehyde (304 mg)
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with water and brine in that order
  4. dry with materialdried over anhydrous sodium sulfate
  5. customAfter evaporation of the solvent under a reduced pressure
  6. customthe resulting residue was purified by a silica gel column chromatography (eluent: hexane/ethyl acetate)

Sources & evidence

ORD record
ord-d6b2ca66178d4359bfa6a04491908642
Source dataset
uspto-grants-2002_05
Patent number
US06387938B1

Reaction notes

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