Methanol → HCID 70561242, compound

HRID 623827Notes

Reaction equation

HRID 623827 reaction equation
[CH3:1][S:2]([C:5]1[CH:6]=[C:7]([C:15]2[N:19]=[CH:18][N:17](/[CH:20]=[CH:21]\[C:22]([O:24]C(C)C)=[O:23])[N:16]=2)[CH:8]=[C:9]([C:11]([F:14])([F:13])[F:12])[CH:10]=1)(=[O:4])=[O:3].O.[Li+].[OH-].CO>C1COCC1.ClCCl>[CH3:1][S:2]([C:5]1[CH:6]=[C:7]([C:15]2[N:19]=[CH:18][N:17](/[CH:20]=[CH:21]\[C:22]([OH:24])=[O:23])[N:16]=2)[CH:8]=[C:9]([C:11]([F:13])([F:12])[F:14])[CH:10]=1)(=[O:4])=[O:3]

Participants

7

Reactant 4

HCID 887MethanolHCID 962WaterHCID 3939Lithium HydroxideHCID 66996153HCID 66996153, compound

Product 1

HCID 70561242HCID 70561242, compoundYield 86.1%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

In a 1-neck 25 mL round-bottomed flask, (Z)-isopropyl 3-(3-(3-(methylsulfonyl)-5-(trifluoromethyl)phenyl)-1H-1,2,4-triazol-1-yl)acrylate (0.350 g, 1.0 eq.), was dissolved in THF (3.5 mL, 5 vol.), added water (3.5 mL, 3.5 Vol) and added LiOH (0.053 g, 1.5 eq.). Reaction mixture was stirred at RT for 2-3 hrs. The progress of the reaction was followed by TLC analysis on silica gel with 10% methanol: dichloromethane as mobile phase and visualization with UV, SM Rf=0.35 and Product Rf=0.15. Reaction mixture was quenched into the acidic ice-water slurry (30 mL) and extracted in the ethyl acetate (25 mL×3). Organic layer was washed with sodium bicarbonate solution (50 mL) followed by drying using anhydrous sodium sulphate. Organic layer was concentrated under reduced pressure to afford 270 mg of crude compound. The resulting crude compound off white was used for further stage, yield (83%); Mass: (ES+) 361.8 (M+1).

Workup

  1. customReaction mixture
  2. customReaction mixture
  3. customwas quenched into the acidic ice-water slurry (30 mL)
  4. extractionextracted in the ethyl acetate (25 mL×3)
  5. washOrganic layer was washed with sodium bicarbonate solution (50 mL)
  6. customby drying
  7. concentrationOrganic layer was concentrated under reduced pressure

Sources & evidence

ORD record
ord-c183ab19107c46b4824f9e8d3ae72fda
Source dataset
uspto-grants-2016_04
Patent number
US09303000B2

Reaction notes

Loading…