(1,1'-Biphenyl)-4-carbonitrile → 2,4-Bisbiphenyl-4-yl-6-(4-bromophenyl)-1,3,5-triazine

HRID 1628367Notes

Reaction equation

HRID 1628367 reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].[Br:5][C:6]1[CH:14]=[CH:13][C:9]([C:10](Cl)=O)=[CH:8][CH:7]=1.[C:15]([C:17]1[CH:22]=[CH:21][C:20]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)=[CH:19][CH:18]=1)#[N:16].S(Cl)(Cl)=O.[Cl-].[NH4+:34]>ClC1C=CC=CC=1Cl.CO>[C:20]1([C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=2)[CH:21]=[CH:22][C:17]([C:15]2[N:16]=[C:15]([C:17]3[CH:22]=[CH:21][C:20]([C:23]4[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=4)=[CH:19][CH:18]=3)[N:34]=[C:10]([C:9]3[CH:13]=[CH:14][C:6]([Br:5])=[CH:7][CH:8]=3)[N:16]=2)=[CH:18][CH:19]=1

Participants

8

Reactant 5

HCID 18021(1,1'-Biphenyl)-4-carbonitrileHCID 24386Thionyl ChlorideHCID 25517Ammonium ChlorideHCID 685154-Bromobenzoyl chlorideHCID 6451240Aluminum(III) Chloride

Product 1

HCID 673352762,4-Bisbiphenyl-4-yl-6-(4-bromophenyl)-1,3,5-triazine

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 72391,2-DichlorobenzeneSolvent

Procedure

1.21 g (0.0091 mol) of aluminium chloride, 1.997 g (0.0091 mol) of 4-bromobenzoyl chloride and 3.42 g (0.01911 mol) of 4-cyanobiphenyl are initially introduced. The solids are dissolved in 80 ml of 1,2-dichlorobenzene. 0.2 ml (0.00274 mol) of thionyl chloride is added. The reaction is carried out at 120° C. for 24 h. After a reaction time of 1 h, 0.9736 g (0.00182 mol) of ammonium chloride is added. As work-up, the mixture is poured into 50 ml of methanol. The white solid is filtered off with suction and recrystallised in chloroform/ethanol. 1.7 g (34%) of clean substance are isolated.

Workup

  1. filtrationThe white solid is filtered off with suction
  2. customrecrystallised in chloroform/ethanol
  3. custom1.7 g (34%) of clean substance are isolated

Sources & evidence

ORD record
ord-b14db8d517f945cdb0d42715f15623d6
Source dataset
uspto-grants-2014_07
Patent number
US08786181B2

Reaction notes

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