Potassium Iodide → 61300-22-9

HRID 616993Notes

Reaction equation

HRID 616993 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([C:15]3[CH:20]=[CH:19][C:18]([F:21])=[CH:17][CH:16]=3)[CH2:13][CH2:12][CH:11](Cl)[CH:10]=[CH:9]2)=[CH:4][CH:3]=1.[NH:22]1[CH2:27][CH2:26][CH:25]([N:28]2[C:32]3[CH:33]=[CH:34][C:35]([Cl:37])=[CH:36][C:31]=3[NH:30][C:29]2=[O:38])[CH2:24][CH2:23]1.C(=O)([O-])[O-].[K+].[K+].[I-].[K+]>O.CN(C)C=O>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2([C:15]3[CH:20]=[CH:19][C:18]([F:21])=[CH:17][CH:16]=3)[CH2:13][CH2:12][CH:11]([N:22]3[CH2:23][CH2:24][CH:25]([N:28]4[C:32]5[CH:33]=[CH:34][C:35]([Cl:37])=[CH:36][C:31]=5[NH:30][C:29]4=[O:38])[CH2:26][CH2:27]3)[CH:10]=[CH:9]2)=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 1046075-Chloro-1,3-dihydro-1-(4-piperidinyl)-2H-benzimidazol-2-oneHCID 133641472~4~-Chloro-1~4~,3~4~-difluoro-2~3~,2~4~-dihydro-2~2~H-1~1~,2~1~:2~1~,3~1~-terphenyl

Product 1

HCID 304589961300-22-9

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of 6.1 g of 4,4-bis(p-fluorophenyl)-1-chloro-2-cyclohexene (m.p. 39°-42° C), 5.0 g of 1-(4-piperidyl)-5-chloro-2-benzimidazolinone, 2.8 g of potassium carbonate, 3.3 g of potassium iodide and 50 ml of dimethylformamide is stirred at 65°-70° C for 3 hours. The reaction mixture is poured into water, and the precipitated powder is collected by filtration, dried and dissolved in a mixture of chloroform and methanol (9:1). The solvent is then removed, and the precipitate is collected by filtration and purified in the same manner to give 1-[1-(4,4-bis(p-fluorophenyl)-2-cyclohexenyl)-4-piperidyl]-5-chloro-2-benzimidazolinone as white crystalline powder, melting at 153°-157° C. This white crystalline powder, when recrystallized from a mixture of ethanol and methanol (7:3), turns into white crystals showing a melting point of 217°-219° C.

Workup

  1. filtrationthe precipitated powder is collected by filtration
  2. customdried
  3. dissolutiondissolved in a mixture of chloroform and methanol (9:1)
  4. customThe solvent is then removed
  5. filtrationthe precipitate is collected by filtration
  6. custompurified in the same manner

Sources & evidence

ORD record
ord-c46868306aba4bd886e68751283c1f90
Source dataset
uspto-grants-1978_02
Patent number
US04076821

Reaction notes

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