Hydrochloric Acid → HCID 86730373, compound

HRID 1465892Notes

Reaction equation

HRID 1465892 reaction equation
[Cl:1][C:2]1[C:7]([C:8]([F:11])([F:10])[F:9])=[CH:6][C:5]([C:12]2[N:16]=[CH:15][N:14](/[CH:17]=[CH:18]\[C:19]([O:21]C(C)C)=[O:20])[N:13]=2)=[CH:4][C:3]=1[C:25]([F:28])([F:27])[F:26].C1COCC1.[Li+].[OH-].Cl>O>[Cl:1][C:2]1[C:7]([C:8]([F:9])([F:11])[F:10])=[CH:6][C:5]([C:12]2[N:16]=[CH:15][N:14](/[CH:17]=[CH:18]\[C:19]([OH:21])=[O:20])[N:13]=2)=[CH:4][C:3]=1[C:25]([F:26])([F:27])[F:28]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 8028TetrahydrofuranHCID 86730372HCID 86730372, compound

Product 1

HCID 86730373HCID 86730373, compoundYield 66.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

A 25-mL, 3-necked, round-bottomed flask was charged with a solution of (Z)-isopropyl 3-(3-(4-chloro-3,5-bis(trifluoromethyl)phenyl)-1H-1,2,4-triazol-1-yl)acrylate (1.33 g) in 1:1 THF:water (26 mL). The solution was treated with solid LiOH (0.53 g, 4 eq.) and stirred at room temperature for 4 h before being diluted with 400 ml water, acidified to pH=2-3 with dilute aqueous HCl, and extracted with EtOAc (3×100 mL). The combined organic extracts were washed with brine, dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure to afford 0.8 g of crude compound (yield: 66%).

Workup

  1. extractionextracted with EtOAc (3×100 mL)
  2. washThe combined organic extracts were washed with brine
  3. dry with materialdried over anhydrous Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-b394054dbc4842e6ae299a4343bf431a
Source dataset
uspto-grants-2015_04
Patent number
US08999996B2

Reaction notes

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