Pyridine → 2-(4-Chlorophenyl)-2-[(1,2,4-triazol-1-yl)methyl]hexyl acrylate

HRID 54908Notes

Reaction equation

HRID 54908 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([CH2:15][N:16]2[CH:20]=[N:19][CH:18]=[N:17]2)([CH2:11][CH2:12][CH2:13][CH3:14])[CH2:9][OH:10])=[CH:4][CH:3]=1.N1C=CC=CC=1.[C:27](Cl)(=[O:30])[CH:28]=[CH2:29].CN(C)C=O>O1CCCC1>[C:27]([O:10][CH2:9][C:8]([C:5]1[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=1)([CH2:15][N:16]1[CH:20]=[N:19][CH:18]=[N:17]1)[CH2:11][CH2:12][CH2:13][CH3:14])(=[O:30])[CH:28]=[CH2:29]

Participants

6

Reactant 4

HCID 1049PyridineHCID 6228DimethylformamideHCID 13140Acryloyl chloride2×HCID 157666652-(4-Chlorophenyl)-2-[(1,2,4-triazol-1-yl)methyl]hexan-1-ol

Product 1

HCID 540337182-(4-Chlorophenyl)-2-[(1,2,4-triazol-1-yl)methyl]hexyl acrylateYield 50.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a 100 mL flask stirring under nitrogen was charged 2.88 g (0.0098 mole) of 2-(4-chlorophenyl)-2-[(1,2,4-triazol-1-yl)methyl]hexan-1-ol in 25 mL of tetrahydrofuran. To the mixture was added 2.5 mL of pyridine followed by 1.0 g (0.011 mole) of acryloyl chloride after which a precipitate formed. The reaction was monitored by GLC and was 60% complete after 1 hour. An additional 1.0 g of acryloyl chloride was added followed by 20 mL of dimethylformamide. The reaction was stirred at 60° C. until the precipitate dissolved and was then stirred overnight at room temperature. The reaction was quenched with 20 mL water and extracted with 10 mL ethyl acetate, washed with 2×10 mL water and 2×20 mL saturated sodium bicarbonate. The solvent was dried and concentrated; the residue was chromatographed on 50 g of silica gel. The product was eluted with a 1 to 1 mixture of hexane and ethyl acetate and gave 1.72 g (50.4% yield) of an oil.

Workup

  1. customformed
  2. customcomplete after 1 hour
  3. stirringThe reaction was stirred at 60° C. until the precipitate
  4. dissolutiondissolved
  5. stirringwas then stirred overnight at room temperature
  6. customThe reaction was quenched with 20 mL water
  7. extractionextracted with 10 mL ethyl acetate
  8. washwashed with 2×10 mL water and 2×20 mL saturated sodium bicarbonate
  9. customThe solvent was dried
  10. concentrationconcentrated
  11. customthe residue was chromatographed on 50 g of silica gel
  12. washThe product was eluted with a 1 to 1 mixture of hexane and ethyl acetate

Sources & evidence

ORD record
ord-bb43c67d0d154e688206712b93d08ba3
Source dataset
uspto-grants-1997_04
Patent number
US05624916

Reaction notes

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