Lithium hydroxide, monohydrate → HCID 178506308, compound

HRID 2262528Notes

Reaction equation

HRID 2262528 reaction equation
COC([C:5]1[NH:6][CH:7]=[C:8]([C:10]2[C:11]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)=[N:12][O:13][C:14]=2[C:15]([F:18])([F:17])[F:16])[N:9]=1)=O.O.[OH-].[Li+]>C1COCC1.O.Cl.CO>[NH:6]1[CH:7]=[C:8]([C:10]2[C:11]([C:19]3[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=3)=[N:12][O:13][C:14]=2[C:15]([F:18])([F:16])[F:17])[N:9]=[CH:5]1

Participants

7

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 1784990604-(3-phenyl-5-trifluoromethyl-isoxazol-4-yl)-1H-imidazole-2-carboxylic acid methyl ester

Product 1

HCID 178506308HCID 178506308, compoundYield 85%

Reagents, catalysts & solvents 4

HCID 313Hydrochloric AcidCatalystHCID 887MethanolCatalystHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-(3-phenyl-5-trifluoromethyl-isoxazol-4-yl)-1H-imidazole-2-carboxylic acid methyl ester (100 mg, 0.3 mmol) in THF (1 mL) was added a solution of lithium hydroxide monohydrate (24.8 mg, 0.6 mmol) in water (1 mL) and the resulting mixture stirred at room temperature overnight, and then at 50° C. overnight. After cooling to room temperature the mixture was acidified to pH 1 with HCl (25%, 3 drops) and methanol (2 drops) added. The mixture was then heated at 80° C. for 34 h and left at room temperature for 2 days. The mixture was then extracted with ethyl acetate and the combined organic extracts washed with an aqueous saturated sodium hydrogen carbonate solution, brine, dried over sodium sulfate and evaporated to afford the title compound (70 mg, 85%) which was obtained as an off-white solid. MS: m/e 280.1 [M+H]+.

Workup

  1. customat 50° C.
  2. customovernight
  3. temperatureAfter cooling to room temperature the mixture
  4. additionadded
  5. temperatureThe mixture was then heated at 80° C. for 34 h
  6. waitleft at room temperature for 2 days
  7. extractionThe mixture was then extracted with ethyl acetate
  8. washthe combined organic extracts washed with an aqueous saturated sodium hydrogen carbonate solution, brine
  9. dry with materialdried over sodium sulfate
  10. customevaporated

Sources & evidence

ORD record
ord-fb01c843581a4f7b9c0de8ff0a829fbf
Source dataset
uspto-grants-2010_12
Patent number
US07851469B2

Reaction notes

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