Hydrochloric Acid → HCID 178494666, compound

HRID 1487823Notes

Reaction equation

HRID 1487823 reaction equation
[CH3:1][O:2][CH2:3][C:4]1[NH:5][C:6]([C:10]2[C:11]([CH3:21])=[CH:12][C:13]([CH3:20])=[C:14]([CH:19]=2)[C:15]([O:17]C)=[O:16])=[C:7]([CH3:9])[N:8]=1.[OH-].[Na+].Cl>CO.O>[CH3:1][O:2][CH2:3][C:4]1[NH:5][C:6]([C:10]2[C:11]([CH3:21])=[CH:12][C:13]([CH3:20])=[C:14]([CH:19]=2)[C:15]([OH:17])=[O:16])=[C:7]([CH3:9])[N:8]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 178494667HCID 178494667, compound2×

Product 1

HCID 178494666HCID 178494666, compoundYield 98.1%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
40 °C

Procedure

Into a 50-mL round-bottom flask, was placed a solution of methyl 5-(2-(methoxymethyl)-4-methyl-1H-imidazol-5-yl)-2,4-dimethylbenzoate (compound 2.1, 150 mg, 0.52 mmol) in methanol (15 mL) and H2O (5 mL). Sodium hydroxide (280 mg, 7.00 mmol) was added and the resulting solution was stirred at 40° C. for 15 h. After cooled to room temperature, the solution was adjusted to pH 5 with aqueous HCl (2 M) and the resulting mixture was concentrated under reduced pressure. The residue was dissolved in methanol (5 mL) and the solids were filtered off. The filtrate was concentrated under reduced pressure to yield the title compound as a light yellow solid (140 mg, crude), which was used in the next step without further purification.

Workup

  1. customInto a 50-mL round-bottom flask, was placed
  2. temperatureAfter cooled to room temperature
  3. concentrationthe resulting mixture was concentrated under reduced pressure
  4. dissolutionThe residue was dissolved in methanol (5 mL)
  5. filtrationthe solids were filtered off
  6. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-acbae4e2a0354338a86694dfb2596acb
Source dataset
uspto-grants-2016_08
Patent number
US09428502B2

Reaction notes

Loading…