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(1,1'-Biphenyl)-4-carbonitrile → Hexachloroantimonate

HRID 2273503
Notes
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Reaction equation

HRID 2273503 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([Br:11])[CH:10]=1)[C:5]([Cl:7])=[O:6].[C:12]1([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH:17]=[CH:16][C:15]([C:18]#[N:19])=[CH:14][CH:13]=1.[Sb:26]([Cl:31])([Cl:30])([Cl:29])([Cl:28])[Cl:27]>C(Cl)(Cl)Cl>[C:12]1([C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)[CH:13]=[CH:14][C:15]([C:18]2[N:19]=[C:18]([C:15]3[CH:16]=[CH:17][C:12]([C:20]4[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=4)=[CH:13][CH:14]=3)[O+:6]=[C:5]([C:4]3[CH:3]=[C:2]([Br:1])[CH:10]=[C:9]([Br:11])[CH:8]=3)[N:19]=2)=[CH:16][CH:17]=1.[Cl:27][Sb-:26]([Cl:7])([Cl:31])([Cl:30])([Cl:29])[Cl:28]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 18021(1,1'-Biphenyl)-4-carbonitrileHCID 24294Antimony pentachlorideHCID 134505263,5-Dibromobenzoyl chloride

Product 2

HCID 3695004HexachloroantimonateHCID 866699604,6-Bis(4-biphenylyl)-2-(3,5-dibromophenyl)-1,3,5-oxadiazin-1-ium

Reagents, catalysts & solvents 1

HCID 6212
Chloroform
Solvent

Conditions

Temperature
0 °C

Procedure

2.98 g of 3,5-dibromobenzoyl chloride and 3.58 g of 4-biphenylcarbonitrile were dissolved in 40 mL of chloroform. The obtained solution was cooled to 0° C., and 2.99 g of antimony pentachloride was added dropwise to the cooled solution. The obtained mixed liquid was stirred at room temperature for 10 minutes, and then, heated under reflux for 14 hours. The obtained reaction mixture was cooled to room temperature, and then distilled under a reduced pressure to remove chloroform to give 4,6-bis(4-biphenylyl)-2-(3,5-dibromophenyl)-1,3,5-oxadiazin-1-ium=hexachloroantimonate as a red solid.

Workup

  1. additionThe obtained mixed liquid
  2. temperatureheated
  3. temperatureunder reflux for 14 hours
  4. customThe obtained reaction mixture
  5. temperaturewas cooled to room temperature
  6. distillationdistilled under a reduced pressure
  7. customto remove chloroform

Sources & evidence

ORD record
ord-ba1c038a8b024af0ad4acf8aa9882bb3
Source dataset
uspto-grants-2015_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09120773B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes