Hydrochloric Acid → HCID 68062441, compound

HRID 508439Notes

Reaction equation

HRID 508439 reaction equation
[CH3:1][C:2]1[N:3]([C:7]2[CH:25]=[CH:24][C:10]([CH2:11][O:12][C:13]3[CH:23]=[CH:22][C:16]([C:17]([O:19]CC)=[O:18])=[CH:15][CH:14]=3)=[CH:9][CH:8]=2)[CH:4]=[CH:5][N:6]=1.O.[OH-].[Li+].Cl>C1COCC1.CO.O.O>[CH3:1][C:2]1[N:3]([C:7]2[CH:25]=[CH:24][C:10]([CH2:11][O:12][C:13]3[CH:23]=[CH:22][C:16]([C:17]([OH:19])=[O:18])=[CH:15][CH:14]=3)=[CH:9][CH:8]=2)[CH:4]=[CH:5][N:6]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 168937Lithium hydroxide, monohydrate2×HCID 66667704HCID 66667704, compound

Product 1

HCID 68062441HCID 68062441, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 21892291Methanol tetrahydrofuran waterSolvent

Procedure

To a solution of ethyl 4-{[4-(2-methyl-1H-imidazol-1-yl)benzyl]oxy}benzoate (Preparation 30, 507 mg, 1.9 mmol) in THF/MeOH/Water (3:3:1, 7 mL) was added lithium hydroxide monohydrate (198 mg, 4.9 mmol) the resulting reaction mixture was heated under reflux for 72 hours. Lithium hydroxide monohydrate (100 mg, 2.5 mmol) was added and the reaction mixture heated at reflux for further 3 hours. The solvent was reduced in vacuo and the residue diluted with water. The resulting aqueous mixture was acidified with 0.2 M aqueous hydrochloric acid to pH 6.5 and the solid precipitate was collected, washed with water and diethyl ether and dried under reduced pressure at 50° C. to yield the title compound as a white solid, which was carried through to the next step without further purification.

Workup

  1. customthe resulting reaction mixture
  2. temperaturewas heated
  3. temperatureunder reflux for 72 hours
  4. temperaturethe reaction mixture heated
  5. temperatureat reflux for further 3 hours
  6. customthe solid precipitate was collected
  7. washwashed with water and diethyl ether
  8. customdried under reduced pressure at 50° C.

Sources & evidence

ORD record
ord-08548f35ee2c4ad08c39e161a60b16a0
Source dataset
uspto-grants-2015_08
Patent number
US09096500B2

Reaction notes

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