Hydrochloric Acid → HCID 178432712, compound

HRID 1487820Notes

Reaction equation

HRID 1487820 reaction equation
[CH3:1][C:2]1[NH:3][C:4]([C:8]2[C:9]([CH3:19])=[CH:10][C:11]([CH3:18])=[C:12]([CH:17]=2)[C:13]([O:15]C)=[O:14])=[C:5]([CH3:7])[N:6]=1.[OH-].[Na+].Cl>CO.O>[CH3:1][C:2]1[NH:3][C:4]([C:8]2[C:9]([CH3:19])=[CH:10][C:11]([CH3:18])=[C:12]([CH:17]=2)[C:13]([OH:15])=[O:14])=[C:5]([CH3:7])[N:6]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 178497363HCID 178497363, compound2×

Product 1

HCID 178432712HCID 178432712, compoundYield 98.8%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
55 °C

Procedure

Into a 50-mL round-bottom flask, were placed methyl 5-(2,4-dimethyl-1H-imidazol-5-yl)-2,4-dimethylbenzoate (compound 1.7, 300 mg, 1.16 mmol) and sodium hydroxide (465 mg, 11.6 mmol) in methanol (20 mL) and H2O (5 mL). The resulting solution was stirred at 55° C. for 4 h, then after cooling to room temperature, aqueous HCl (2 M) was added to adjust the pH to 5. The resulting mixture was concentrated under reduced pressure and the residue was dissolved in methanol (5 mL). The solids were removed by filtration and the filtrate was concentrated under reduced pressure to yield the title compound as a light yellow solid (280 mg, crude), which was used in the next step without further purification.

Workup

  1. customInto a 50-mL round-bottom flask, were placed
  2. temperatureafter cooling to room temperature
  3. concentrationThe resulting mixture was concentrated under reduced pressure
  4. dissolutionthe residue was dissolved in methanol (5 mL)
  5. customThe solids were removed by filtration
  6. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-5cb10432d3894dfab688504cda8b46d6
Source dataset
uspto-grants-2016_08
Patent number
US09428502B2

Reaction notes

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