Imidazole → HCID 67808941, compound

HRID 1737868Notes

Reaction equation

HRID 1737868 reaction equation
[NH:1]1[CH:5]=[CH:4][N:3]=[CH:2]1.O=S(Cl)Cl.[C:10]([C:12]1[CH:17]=[CH:16][C:15]([C:18](=O)[CH2:19][CH2:20][C:21]2[CH:26]=[CH:25][C:24]([F:27])=[CH:23][CH:22]=2)=[CH:14][CH:13]=1)#[N:11].C(Cl)Cl>O1CCCC1>[C:10]([C:12]1[CH:13]=[CH:14][C:15]([C:18]([N:1]2[CH:5]=[CH:4][N:3]=[CH:2]2)=[CH:19][CH2:20][C:21]2[CH:22]=[CH:23][C:24]([F:27])=[CH:25][CH:26]=2)=[CH:16][CH:17]=1)#[N:11]

Participants

6

Reactant 4

HCID 795ImidazoleHCID 6344DichloromethaneHCID 24386Thionyl ChlorideHCID 218435754-[3-(4-Fluorophenyl)propanoyl]benzonitrile

Product 1

HCID 67808941HCID 67808941, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Imidazole (0.55 g, 8 mmol) is dissolved in dry tetrahydrofuran. The solution is cooled on icebath and SOCl2 (0.16 ml, 2 mmol) is added dropwise to the cooled solution. The mixture is stirred for 10 min. 1-(4-cyanophenyl)-3-(4-fluorophenyl)-1-propanone (0.34 g, 1.3 mmol) is added and the mixture is stirred in room temperature for 4 days. Methylene chloride is added and tie mixture is washed with water. The organic layer is dried and the solvent is evaporated. The residue contains 35% of the product (1H NMR) as a 9:1 mixture of the isomers. The product is purified by flash chromatography (eluent CH2Cl2 -MeOH 99:1).

Workup

  1. additionis added dropwise to the cooled solution
  2. stirringthe mixture is stirred in room temperature for 4 days
  3. washtie mixture is washed with water
  4. customThe organic layer is dried
  5. customthe solvent is evaporated
  6. additionas a 9:1 mixture of the isomers
  7. customThe product is purified by flash chromatography (eluent CH2Cl2 -MeOH 99:1)

Sources & evidence

ORD record
ord-5dc011cb8ce84fd98a5280a94479f828
Source dataset
uspto-grants-1999_10
Patent number
US05962495

Reaction notes

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