Dimethyl Sulfoxide → 4'-Formyl-[1,1'-biphenyl]-2-carbonitrile

HRID 1739066Notes

Reaction equation

HRID 1739066 reaction equation
C(Cl)(=O)C(Cl)=O.CS(C)=O.[OH:11][CH2:12][C:13]1[CH:18]=[CH:17][C:16]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=2[C:25]#[N:26])=[CH:15][CH:14]=1.C(N(CC)CC)C>C(Cl)Cl.O>[C:25]([C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][C:19]=1[C:16]1[CH:15]=[CH:14][C:13]([CH:12]=[O:11])=[CH:18][CH:17]=1)#[N:26]

Participants

7

Reactant 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 13938962-[4-(Hydroxymethyl)phenyl]benzonitrile

Product 1

HCID 13940624'-Formyl-[1,1'-biphenyl]-2-carbonitrile

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent3×

Procedure

53 ml of oxalyl chloride in 2 litres of methylene chloride are cooled to -60°. A solution of 88 ml of dimethyl sulfoxide in 150 ml of methylene chloride is added dropwise at this temperature and the mixture is then stirred for 2 minutes. After this, 117 g of 4-hydroxymethyl-2'-cyanobiphenyl in 1 litre of methylene chloride are added dropwise at -60°. After addition has ended (about 5 minutes), the mixture is subsequently stirred for 15 minutes. After this, 390 ml of triethylamine are added dropwise. The mixture is then stirred at -60° for 2 minutes and allowed to wann to room temperature. The reaction mixture is poured into water, extracted with methylene chloride, and the organic phase is washed with dilute hydrochloric acid and brine, dried and concentrated. The product is stirred in hexane, filtered off with suction, washed and dried at 600 in a high vacuum. Elemental analysis: C 80.7%, H 4.5%, N 6.7%, O 7.7%.

Workup

  1. additionAfter addition
  2. custom(about 5 minutes)
  3. stirringthe mixture is subsequently stirred for 15 minutes
  4. stirringThe mixture is then stirred at -60° for 2 minutes
  5. customto wann to room temperature
  6. extractionextracted with methylene chloride
  7. washthe organic phase is washed with dilute hydrochloric acid and brine
  8. customdried
  9. concentrationconcentrated
  10. stirringThe product is stirred in hexane
  11. filtrationfiltered off with suction
  12. washwashed
  13. customdried at 600 in a high vacuum

Sources & evidence

ORD record
ord-2c4db3dcf3bf4f6a8a9608e53617ae59
Source dataset
uspto-grants-1999_10
Patent number
US05965592

Reaction notes

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