Water → HCID 20312714, compound

HRID 2420054Notes

Reaction equation

HRID 2420054 reaction equation
[OH:1][C:2]1[C:7]([C:8]2[C:13]([OH:14])=[CH:12][CH:11]=[C:10]([C:15]#[N:16])[CH:9]=2)=[CH:6][C:5]([C:17]#[N:18])=[CH:4][CH:3]=1.C(=O)([O-])[O-].[Na+].[Na+].Br[CH2:26][CH2:27]Br.O>CN(C)C=O>[CH:6]1[C:7]2[C:8]3[CH:9]=[C:10]([C:15]#[N:16])[CH:11]=[CH:12][C:13]=3[O:14][CH2:27][CH2:26][O:1][C:2]=2[CH:3]=[CH:4][C:5]=1[C:17]#[N:18]

Participants

6

Reactant 4

HCID 962WaterHCID 78391,2-DibromoethaneHCID 10340Sodium CarbonateHCID 20312716HCID 20312716, compound

Product 1

HCID 20312714HCID 20312714, compoundYield 29.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
150 °C

Procedure

A mixture of 6,6'-dihydroxy[1,1'biphenyl]-3,3'-dicarbonitrile (11.8 g), sodium carbonate (10.6 g), and 1,2-dibromoethane (8.4 g) in 250 ml of anhydrous dimethylformamide is heated at 150° C for 18 hours under nitrogen. The reaction mixture is poured into water and extracted with three 200 ml portions of dichloromethane. The dichloromethane extracts are combined and washed with 10% sodium hydroxide, water, and brine. The solution is filtered through 100 ml of silica gel and concentrated. The resultant solid is recrystallized from benzene to yield 3.5 g of the title compound, melting point 195-196° C.

Workup

  1. extractionextracted with three 200 ml portions of dichloromethane
  2. washwashed with 10% sodium hydroxide, water, and brine
  3. filtrationThe solution is filtered through 100 ml of silica gel
  4. concentrationconcentrated
  5. customThe resultant solid is recrystallized from benzene

Sources & evidence

ORD record
ord-ddac1dc0af21481bbbe6775c2250b181
Source dataset
uspto-grants-1978_08
Patent number
US04108894

Reaction notes

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