Benzoyl chloride → HCID 9864577, compound

HRID 2307866Notes

Reaction equation

HRID 2307866 reaction equation
[C:1](Cl)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.N[S:11][C:12]#[N: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:13][C:12]([NH:29][C:26]1[CH:25]=[CH:24][C:23]([CH:19]([N:14]2[CH:18]=[CH:17][N:16]=[CH:15]2)[CH:20]([CH3:22])[CH3:21])=[CH:28][CH:27]=1)=[S:11])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 7412Benzoyl chlorideHCID 519457HCID 519457, compoundHCID 22335511HCID 22335511, compound

Product 1

HCID 9864577HCID 9864577, compoundYield 72.1%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent2×

Conditions

Temperature
80 °C

Procedure

Benzoyl chloride (0.067 mol) was added to a solution of aminothiocyanate (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 off 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 the solvent evaporated, yielding 15.2 g (72%) of (±)-N-benzoyl-N′-[4-[1-(1H-imidazol-1-yl)-2-methylpropyl]phenyl]thiourea (interm. 1).

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 off
  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. customthe solvent evaporated

Sources & evidence

ORD record
ord-765b49c91a1445f4bfb2483d4f3561a3
Source dataset
uspto-grants-2004_12
Patent number
US06833375B2

Reaction notes

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