Sodium Hydroxide → HCID 178424705, compound

HRID 541247Notes

Reaction equation

HRID 541247 reaction equation
[CH3:1][C:2]1[CH:11]=[C:10]([CH3:12])[C:9]([C:13]2[NH:17][C:16]([CH2:18][CH:19]3[CH2:23][CH2:22][O:21][CH2:20]3)=[N:15][N:14]=2)=[CH:8][C:3]=1[C:4]([O:6]C)=[O:5].[OH-].[Na+]>CO.O>[CH3:1][C:2]1[CH:11]=[C:10]([CH3:12])[C:9]([C:13]2[NH:17][C:16]([CH2:18][CH:19]3[CH2:23][CH2:22][O:21][CH2:20]3)=[N:15][N:14]=2)=[CH:8][C:3]=1[C:4]([OH:6])=[O:5]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 178497401HCID 178497401, compound2×

Product 1

HCID 178424705HCID 178424705, compoundYield 87.3%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
70 °C

Procedure

To a round-bottom flask was added a solution of methyl 2,4-dimethyl-5-(5-((tetrahydrofuran-3-yl)methyl)-4H-1,2,4-triazol-3-yl)benzoate (compound 130.5, 600 mg, 1.90 mmol, 1.00 equiv) in methanol (10 mL). A solution of sodium hydroxide (381 mg, 9.53 mmol, 5.00 equiv) in water (5 mL) was added and the resulting mixture was stirred for 3 h at 70° C. in an oil bath. After cooling to room temperature, the organic solvent was then removed under reduced pressure and the pH of the remaining aqueous phase was adjusted to 3-4 with hydrogen chloride (aq., 1 M). The resulting solids were collected via filtration and dried in an oven under reduced pressure to yield 0.500 g (87%) of the title compound as a yellow solid.

Workup

  1. temperatureAfter cooling to room temperature
  2. customthe organic solvent was then removed under reduced pressure
  3. filtrationThe resulting solids were collected via filtration
  4. customdried in an oven under reduced pressure

Sources & evidence

ORD record
ord-99e826cf70484ebab3380e4ebece597c
Source dataset
uspto-grants-2014_10
Patent number
US08871790B2

Reaction notes

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