Potassium thiocyanate → 4-(2-Chloropyridin-4-yl)-5-(4-fluorophenyl)-1,3-dihydroimidazole-2-thione

HRID 730051Notes

Reaction equation

HRID 730051 reaction equation
Cl.[NH2:2][CH:3]([C:13]1[CH:18]=[CH:17][N:16]=[C:15]([Cl:19])[CH:14]=1)[C:4]([C:6]1[CH:11]=[CH:10][C:9]([F:12])=[CH:8][CH:7]=1)=O.[S-:20][C:21]#[N:22].[K+]>CN(C=O)C.O>[Cl:19][C:15]1[CH:14]=[C:13]([C:3]2[NH:2][C:21](=[S:20])[NH:22][C:4]=2[C:6]2[CH:11]=[CH:10][C:9]([F:12])=[CH:8][CH:7]=2)[CH:18]=[CH:17][N:16]=1

Participants

5

Reactant 2

HCID 516872Potassium thiocyanateHCID 86760946HCID 86760946, compound

Product 1

HCID 108597274-(2-Chloropyridin-4-yl)-5-(4-fluorophenyl)-1,3-dihydroimidazole-2-thione

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 6228DimethylformamideSolvent

Procedure

With gentle heating, 23a (2.9 g; about 9.6 mmol) was dissolved in absolute DMF (75 ml). Potassium thiocyanate (1.9 g; 19.6 mmol) was introduced into the clear orange-red solution: immediate opalescence and a lighter color. The reaction mixture was stirred under reflux for 1.5 h. The suspension was cooled to room temperature and, with H2O cooling, diluted dropwise with H2O (about 140 ml). The yellow precipitate was filtered off, washed with H2O and dried under reduced pressure over CaCl2.

Workup

  1. temperatureunder reflux for 1.5 h
  2. filtrationThe yellow precipitate was filtered off
  3. washwashed with H2O
  4. dry with materialdried under reduced pressure over CaCl2

Sources & evidence

ORD record
ord-fafc5c2787c2404e8e8b131a28da6adc
Source dataset
uspto-grants-2009_09
Patent number
US07582660B2

Reaction notes

Loading…