Dabco → (Z)-isopropyl 3-(3-(3,5-bis(trifluoromethyl)phenyl)-1H-1,2,4-triazol-1-yl)acrylate

HRID 1486964Notes

Reaction equation

HRID 1486964 reaction equation
[F:1][C:2]([F:19])([F:18])[C:3]1[CH:4]=[C:5]([C:13]2[N:17]=[CH:16][NH:15][N:14]=2)[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1.C1N2CCN(CC2)C1.I/[CH:29]=[CH:30]\[C:31]([O:33][CH:34]([CH3:36])[CH3:35])=[O:32]>CN(C=O)C>[F:19][C:2]([F:1])([F:18])[C:3]1[CH:4]=[C:5]([C:13]2[N:17]=[CH:16][N:15](/[CH:29]=[CH:30]\[C:31]([O:33][CH:34]([CH3:36])[CH3:35])=[O:32])[N:14]=2)[CH:6]=[C:7]([C:9]([F:10])([F:12])[F:11])[CH:8]=1

Participants

5

Reactant 3

HCID 9237DabcoHCID 585036632-Propenoic acid, 3-iodo-, 1-methylethyl ester, (2Z)-HCID 178506083HCID 178506083, compound

Product 1

HCID 53386343(Z)-isopropyl 3-(3-(3,5-bis(trifluoromethyl)phenyl)-1H-1,2,4-triazol-1-yl)acrylateYield 61.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A 3-neck round-bottom flask was charged with a solution of 3-(3,5-bis(trifluoromethyl)phenyl)-1H-1,2,4-triazole (2) (160 g, 1.0 eq.) in DMF (960 mL). The solution was treated DABCO (127.74 g, 2 eq.) and stirred for 30 min before being treated with (Z)-isopropyl 3-iodoacrylate (150.32 g, 1.1 eq.). After 1 hm the reaction mixture was poured into ice water slurry (5 L) and extracted with EtOAc (3×1 L). The combined organic layers were washed with brine (3×100 mL), dried over anhydrous Na2SO4, filtered, and concentrated under reduced pressure to afford 250 g of crude compound. Purification by column chromatography (silica gel, eluting with EtOAc/hexane) afforded 138 g (61% yield) of pure isopropyl ester (3).

Workup

  1. extractionextracted with EtOAc (3×1 L)
  2. washThe combined organic layers were washed with brine (3×100 mL)
  3. dry with materialdried over anhydrous Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customto afford 250 g of crude compound
  7. customPurification
  8. washby column chromatography (silica gel, eluting with EtOAc/hexane)

Sources & evidence

ORD record
ord-df15b83cdeb64afa9e66ae76d0b2a19a
Source dataset
uspto-grants-2016_08
Patent number
US09428490B2

Reaction notes

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