Benzoyl chloride → HCID 9864577, compound

HRID 429862Notes

Reaction equation

HRID 429862 reaction equation
[C:1](Cl)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH4+].[N:11]#[C:12][S-:13].[N:14]1([CH:19]([C:23]2[CH:28]=[CH:27][C:26]([NH2:29])=[CH:25][CH:24]=2)[CH:20]([CH3:22])[CH3:21])[CH:18]=[CH:17][N:16]=[CH:15]1>CC(=O)C>[C:1]([NH:11][C:12]([NH:29][C:26]1[CH:27]=[CH:28][C:23]([CH:19]([N:14]2[CH:18]=[CH:17][N:16]=[CH:15]2)[CH:20]([CH3:22])[CH3:21])=[CH:24][CH:25]=1)=[S:13])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 7412Benzoyl chlorideHCID 15666Ammonium thiocyanateHCID 22335511HCID 22335511, compound

Product 1

HCID 9864577HCID 9864577, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent2×

Conditions

Temperature
80 °C

Procedure

Benzoylchloride (0.067 mol) was added to a solution of NH4SCN (5.09 g) in 2-propanone (150 ml) and the mixture was stirred and refluxed for 20 minutes. A solution of 4-[1-(1H-imidazol-1-yl)-2-methylpropyl]benzenamine (0.0557 mol) in 2-propanone (150 ml) was added and the mixture was stirred and refluxed at 80° C. overnight. The mixture was cooled, filtered through celite and the filtrate was evaporated. The residue was taken up in CH2Cl2. The organic layer was dried, filtered and the solvent evaporated. The residue was purified by column chromatography over silica gel (eluent: CH2Cl2/CH3OH/NH4OH 98/2/0.1). The pure fractions were collected and evaporated. The residue was recrystallized from 2-propanone and DIPE, yielding (±)-N-benzoyl-N′-[4-[1-(1H-imidazol-1-yl)-2-methylpropyl]phenyl]thiourea (compound 698).

Workup

  1. temperaturerefluxed for 20 minutes
  2. stirringthe mixture was stirred
  3. temperatureThe mixture was cooled
  4. filtrationfiltered through celite
  5. customthe filtrate was evaporated
  6. customThe organic layer was dried
  7. filtrationfiltered
  8. customthe solvent evaporated
  9. customThe residue was purified by column chromatography over silica gel (eluent: CH2Cl2/CH3OH/NH4OH 98/2/0.1)
  10. customThe pure fractions were collected
  11. customevaporated
  12. customThe residue was recrystallized from 2-propanone and DIPE

Sources & evidence

ORD record
ord-e5e837a4b55a42789130536b96d75c66
Source dataset
uspto-grants-2001_11
Patent number
US06319939B1

Reaction notes

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