Hydrochloric Acid → HCID 89401938, compound

HRID 1486983Notes

Reaction equation

HRID 1486983 reaction equation
[F:1][C:2]([F:27])([F:26])[C:3]1[CH:4]=[C:5]([C:13]2[N:14]=[CH:15][N:16](/[CH:18]=[CH:19]\[C:20]([O:22]C(C)C)=[O:21])[CH:17]=2)[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1.O.O[Li].O.Cl>C1COCC1.C(OCC)(=O)C.CCCCCC>[F:12][C:9]([F:10])([F:11])[C:7]1[CH:6]=[C:5]([C:13]2[N:14]=[CH:15][N:16](/[CH:18]=[CH:19]\[C:20]([OH:22])=[O:21])[CH:17]=2)[CH:4]=[C:3]([C:2]([F:1])([F:27])[F:26])[CH:8]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 168937Lithium hydroxide, monohydrateHCID 89404248HCID 89404248, compound

Product 1

HCID 89401938HCID 89401938, compoundYield 44.8%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 21226206Ethyl acetate hexaneSolvent

Procedure

In a 50 mL, 3N round-bottomed flask equipped with nitrogen inlet, thermometer pocket and stopper, (Z)-isopropyl 3-(4-(3,5-bis(trifluoromethyl)phenyl)-1H-imidazol-1-yl)acrylate (2) (1.0 g, 1.0 eq.) was dissolved in THF: H2O (20 mL, 1:1, 20V). To this reaction mixture LiOH.H2O (0.535 g, 5.0 eq.) was added at 0° C. This reaction mixture was stirred for 3-4 h and progress of the reaction was followed by TLC using 20% ethyl acetate/n-hexane as mobile phase. Reaction mixture was acidified using dilute HCl. The reaction mixture was extracted with EtOAc (3×20 mL). The combined organic layers was washed with brine solution (3×50 mL), dried over MgSO4, filtered, and concentrated under reduced pressure by rotary evaporation to afford 0.4 g of crude compound which was used for next step without purification.

Workup

  1. customIn a 50 mL, 3N round-bottomed flask equipped with nitrogen inlet
  2. customReaction mixture
  3. extractionThe reaction mixture was extracted with EtOAc (3×20 mL)
  4. washThe combined organic layers was washed with brine solution (3×50 mL)
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure by rotary evaporation

Sources & evidence

ORD record
ord-85b0d052a5174ca6bf771db5733251e2
Source dataset
uspto-grants-2016_08
Patent number
US09428490B2

Reaction notes

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