Water → [1,1'-Biphenyl]-4-carbonitrile, 4'-methoxy-

HRID 1275412Notes

Reaction equation

HRID 1275412 reaction equation
ClC1N=C(Cl)N=C(Cl)N=1.[CH3:10][O:11][C:12]1[CH:17]=[CH:16][C:15]([C:18]2[CH:23]=[CH:22][C:21]([C:24]([NH2:26])=O)=[CH:20][CH:19]=2)=[CH:14][CH:13]=1.O.C(Cl)Cl>CN(C=O)C>[C:24]([C:21]1[CH:20]=[CH:19][C:18]([C:15]2[CH:16]=[CH:17][C:12]([O:11][CH3:10])=[CH:13][CH:14]=2)=[CH:23][CH:22]=1)#[N:26]

Participants

6

Reactant 4

HCID 962WaterHCID 6344DichloromethaneHCID 7954Cyanuric chlorideHCID 153633494-(4-Methoxyphenyl)benzamide

Product 1

HCID 93892[1,1'-Biphenyl]-4-carbonitrile, 4'-methoxy-Yield 72.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A fine suspension of 44.2 g (0.24 mol) of 2,4,6-trichloro-1,3,5-triazine in 190 ml of DMF is added to a suspension of 20 g (0.09 mol) of 4'-methoxy-4-biphenyl carboxamide in 370 ml of DMF and is left under agitation for 20 hours. A mixture of 300 ml water and 200 g crushed ice is added to the reaction medium and extraction is carried out with methylene chloride (3×100 ml). The combined organic extracts are washed with water (2×200 ml), dried over magnesium sulphate, and the solvent is eliminated by distillation under reduced pressure. The dry extract is taken up in 80 ml ethanol and agitation is carried out for 15 minutes, followed by crystallization by the addition of 200 ml of heptane, cooling down to ambient temperature under agitation, drying and washing with heptane. After drying, 13.7 g of 4-cyano-4'-methoxy biphenyl is obtained in the form of a beige powder (yield: 72.5%).

Workup

  1. customcrushed ice
  2. additionis added to the reaction medium and extraction
  3. washThe combined organic extracts are washed with water (2×200 ml)
  4. dry with materialdried over magnesium sulphate
  5. distillationthe solvent is eliminated by distillation under reduced pressure
  6. extractionThe dry extract
  7. waitagitation is carried out for 15 minutes
  8. customfollowed by crystallization by the addition of 200 ml of heptane
  9. customdrying
  10. washwashing with heptane
  11. customAfter drying

Sources & evidence

ORD record
ord-4101c4a0b0d94bce8c46c521297dd55d
Source dataset
uspto-grants-2000_12
Patent number
US06160157

Reaction notes

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