Sodium Hydroxide → HCID 53386231, compound

HRID 623818Notes

Reaction equation

HRID 623818 reaction equation
[CH:1]([O:4][C:5]1[CH:10]=[C:9]([C:11]2[N:15]=[CH:14][NH:13][N:12]=2)[CH:8]=[C:7]([C:16]([F:19])([F:18])[F:17])[N:6]=1)([CH3:3])[CH3:2].[OH-:20].[Na+]>CN(C=O)C.C(OCC)(=O)C.CCCCCC>[CH:1]([O:4][C:5]1[CH:10]=[C:9]([C:11]2[N:15]=[CH:14][N:13](/[CH:9]=[CH:10]\[C:5]([O:4][CH:1]([CH3:3])[CH3:2])=[O:20])[N:12]=2)[CH:8]=[C:7]([C:16]([F:18])([F:17])[F:19])[N:6]=1)([CH3:3])[CH3:2]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 178458205HCID 178458205, compound

Product 1

HCID 53386231HCID 53386231, compoundYield 70.8%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent2×HCID 21226206Ethyl acetate hexaneSolvent

Conditions

Temperature
0 °C

Procedure

In a 50 ml capacity 3-neck round-bottomed flask attached with nitrogen bubbler, & magnetic stirrer 2-isopropoxy-4-(1H-1,2,4-triazol-3-yl)-6-(trifluoromethyl)pyridine (1 g), dissolved in 10 ml DMF at RT. Ethyl iodo acrylate (1.310 g) in DMF (1 ml) dropwise added in the reaction mixture. Then NaOH (0.291 g) added and stirred the reaction mixture for 12 h at 0° C. Completion of the reaction confirmed on TLC in 30% ethyl acetate/hexane mobile phase. Reaction gives two isomeric compounds (cis/trans). The reaction mixture was poured in ice water solution & extract with ethylacetate (3×50 mL). Organic layer dried over Na2SO4 & concentrate to give crude product (1.1 g). The crude reaction mixture was purified by column chromatography using silica 60/120 using ethyl acetate:hexane as mobile phase. The column was packed in hexane and started eluting in ethyl acetate in gradient manner starting with fraction collection (25-mL fractions) from 1% to 5% ethyl acetate in hexane. Compound started eluting with 5% ethyl acetate in hexane. Fractions containing such TLC profile was collected together to obtain pure (Z)-isopropyl 3-(3-(2-isopropoxy-6-(trifluoromethyl)pyridin-4-yl)-1H-1,2,4-triazol-1-yl)acrylate (500 mg).

Workup

  1. customReaction
  2. customgives two isomeric compounds (cis/trans)
  3. extractionextract with ethylacetate (3×50 mL)
  4. dry with materialOrganic layer dried over Na2SO4
  5. concentrationconcentrate
  6. customto give crude product (1.1 g)
  7. customThe crude reaction mixture
  8. customwas purified by column chromatography
  9. washstarted eluting in ethyl acetate in gradient manner
  10. customstarting with fraction collection (25-mL fractions) from 1% to 5% ethyl acetate in hexane
  11. washCompound started eluting with 5% ethyl acetate in hexane
  12. additionFractions containing such TLC profile
  13. customwas collected together

Sources & evidence

ORD record
ord-4b83c075c6eb4b548a760a2accccc53e
Source dataset
uspto-grants-2016_04
Patent number
US09303000B2

Reaction notes

Loading…