Potassium Iodide → HCID 13364149, compound

HRID 616995Notes

Reaction equation

HRID 616995 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.[Br:22][C:23]1[CH:28]=[CH:27][C:26]([N:29]2[C:33]3([CH2:38][CH2:37][NH:36][CH2:35][CH2:34]3)[C:32](=[O:39])[NH:31][CH2:30]2)=[CH:25][CH:24]=1.C(=O)([O-])[O-].[K+].[K+].[I-].[K+]>O.CN(C)C=O>[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]([N:36]3[CH2:35][CH2:34][C:33]4([N:29]([C:26]5[CH:25]=[CH:24][C:23]([Br:22])=[CH:28][CH:27]=5)[CH2:30][NH:31][C:32]4=[O:39])[CH2:38][CH2:37]3)[CH:10]=[CH:9]2)=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 133641431-(4-Bromophenyl)-1,3,8-triazaspiro[4.5]decan-4-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 13364149HCID 13364149, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of 3.7 g of 4,4-bis(p-fluorophenyl)-1-chloro-2-cyclohexene, 3.1 g of 1-(p-bromophenyl)-1,3,8-triazaspiro[4.5]decan-4-one (m.p. 204°-207° C), 1.7 g of potassium carbonate, 2 g of potassium iodide and 25 ml of dimethylformamide is stirred at 65°-75° C for 3.5 hours. The reaction mixture is then poured into water. The precipitated powder is collected by filtration and dissolved in methanol. The solution is concentrated to some degree, and acetone is added thereto, and the whole mixture is cooled. The precipitated crystals are collected by filtration and purified in the same manner to give 8-[4,4-bis(p-fluorophenyl)-2-cyclohexenyl]-1-(p-bromophenyl)-1,3,8-triazaspiro[4.5]decan-4-one as white crystals, melting at 219°-221° C.

Workup

  1. filtrationThe precipitated powder is collected by filtration
  2. dissolutiondissolved in methanol
  3. concentrationThe solution is concentrated to some degree, and acetone
  4. additionis added
  5. temperaturethe whole mixture is cooled
  6. filtrationThe precipitated crystals are collected by filtration
  7. custompurified in the same manner

Sources & evidence

ORD record
ord-e386aa055bd549aeb8f2e1ddcead6155
Source dataset
uspto-grants-1978_02
Patent number
US04076821

Reaction notes

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