Potassium thiocyanate → HCID 178427859, compound

HRID 522473Notes

Reaction equation

HRID 522473 reaction equation
[CH:1]1([C:4](=O)[CH2:5][NH:6][C:7]2[C:8]([CH3:16])=[CH:9][C:10]([F:15])=[C:11]([CH:14]=2)[C:12]#[N:13])[CH2:3][CH2:2]1.[S-:18][C:19]#[N:20].[K+]>C(O)(=O)C>[CH:1]1([C:4]2[N:20]=[C:19]([SH:18])[N:6]([C:7]3[C:8]([CH3:16])=[CH:9][C:10]([F:15])=[C:11]([CH:14]=3)[C:12]#[N:13])[CH:5]=2)[CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 516872Potassium thiocyanateHCID 866912475-[(2-Cyclopropyl-2-oxoethyl)amino]-2-fluoro-4-methylbenzonitrile

Product 1

HCID 178427859HCID 178427859, compoundYield 85.3%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
110 °C

Procedure

5-(2-Cyclopropyl-2-oxoethylamino)-2-fluoro-4-methylbenzonitrile (14.19 g, 61.2 mmol) was dissolved in glacial acetic acid (300 mL). Potassium thiocyanate (11.9 g, 122.4 mmol) was added as a solid with stirring. The reaction mixture was heated to 110° C. for 4 hours at which time the solvent was removed under reduced pressure. The residue was taken up in dichloromethane (200 mL) and washed with 200 mL water. The aqueous extract was extracted with (2×200 mL) additional dichloromethane, the organic extracts combined and dried over magnesium sulfate. The solvent was removed under reduced pressure and the oily residue was re-dissolved in EA (50 mL) and 150 mL hexanes was added. A dark layer formed and a stir bar was added to the flask. Vigorous stirring caused the product to precipitate as a peach colored solid. The product was collected by filtration, to yield 5-(4-cyclopropyl-2-mercapto-1H-imidazol-1-yl)-2-fluoro-4-methylbenzonitrile, (14.26 g, 52.23 mmol). Anal. LC/MS (m/z: 274, M+1)

Workup

  1. customwas removed under reduced pressure
  2. washwashed with 200 mL water
  3. extractionThe aqueous extract
  4. extractionwas extracted with (2×200 mL) additional dichloromethane
  5. dry with materialdried over magnesium sulfate
  6. customThe solvent was removed under reduced pressure
  7. dissolutionthe oily residue was re-dissolved in EA (50 mL)
  8. addition150 mL hexanes was added
  9. customA dark layer formed
  10. additiona stir bar was added to the flask
  11. stirringVigorous stirring
  12. customto precipitate as a peach
  13. filtrationThe product was collected by filtration

Sources & evidence

ORD record
ord-d9ca909805f541b8b1bd2cefb5dc785c
Source dataset
uspto-grants-2016_05
Patent number
US09333197B2

Reaction notes

Loading…