Acrylonitrile → HCID 86614907, compound

HRID 1985862Notes

Reaction equation

HRID 1985862 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:12]([C:13]3[CH:18]=[CH:17][C:16]([CH3:19])=[CH:15][CH:14]=3)[C:11]([SH:20])=[N:10][CH:9]=2)=[CH:4][CH:3]=1.[C:21](#[N:24])[CH:22]=[CH2:23]>O1CCOCC1>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[N:12]([C:13]3[CH:18]=[CH:17][C:16]([CH3:19])=[CH:15][CH:14]=3)[C:11](=[S:20])[N:10]([CH2:23][CH2:22][C:21]#[N:24])[CH:9]=2)=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 7855AcrylonitrileHCID 178426215HCID 178426215, compound

Product 1

HCID 86614907HCID 86614907, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
70 °C

Procedure

A mixture 5-(4-fluorophenyl)-1-p-tolyl-1H-imidazole-2-thiol (1 eq) in dioxane is stirred and Triton B is added. The mixture is heated to 70° C. and acrylonitrile (1 eq) is added and heated for 3 hours. The cooled mixture is partitioned between aqueous 0.1N HCl and ethyl acetate. The organic layer is washed with water and brine, dried over sodium sulfate, filtered and the solvent removed under reduce pressure. Flash chromatography (SiO2) gives 3-(5-(4-fluorophenyl)-1,2-dihydro-2-thioxo-1-p-tolylimidazol-3-yl)propanenitrile.

Workup

  1. additionTriton B is added
  2. temperatureheated for 3 hours
  3. customThe cooled mixture is partitioned between aqueous 0.1N HCl and ethyl acetate
  4. washThe organic layer is washed with water and brine
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. customthe solvent removed

Sources & evidence

ORD record
ord-0da725250010453896f1a69c88e2acd6
Source dataset
uspto-grants-2009_06
Patent number
US07547717B2

Reaction notes

Loading…