p-Toluenesulfonic acid → HCID 20437534, compound

HRID 1980196Notes

Reaction equation

HRID 1980196 reaction equation
[C:1]([CH:3]([C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([O:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[N:6]=1)O)#N.[CH:18]([CH:20]1[CH:22](C(O)=O)[C:21]1([CH3:27])C)=[O:19].C1(C)C=CC(S(O)(=O)=O)=CC=1.[CH:39]1([N:45]=C=NC2CCCCC2)CCCCC1>N1C=CC=CC=1>[C:39]([C:1]1([CH2:3][C:5]2[CH:10]=[CH:9][CH:8]=[C:7]([O:11][C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[N:6]=2)[CH:20]([CH:18]=[O:19])[C:21]1([CH3:27])[CH3:22])#[N:45]

Participants

6

Reactant 4

HCID 6101p-Toluenesulfonic acidHCID 10868DicyclohexylcarbodiimideHCID 1794493-Formyl-2,2-dimethylcyclopropane-1-carboxylic acidHCID 12884337Cyano(6-phenoxy-2-pyridyl)methanol

Product 1

HCID 20437534HCID 20437534, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent2×

Procedure

To a 250 ml round bottom flask was added 6.0 g (26.7 mmol) of cyano(6-phenoxy-2-pyridinyl)methanol, 3.8 g (26.7 mmol) of 3-formyl-2,2-dimethylcyclopropane carboxylic acid and 60 ml of pyridine. The mixture was stirred to assure homogeneity and 0.28 g (1.45 mmol) of p-toluene sulfonic acid was added. Stirring was maintained for 15 minutes and then 6.30 g (30.4 mmol) of dicyclohexyl carbodiimide, dissolved in a minimum amount of pyridine, was added. The reaction mixture was stirred at room temperature for 24 hours. At the completion of this time, the reaction mixture was filtered and then the solvent was removed by evaporation under reduced pressure. The residue was taken up in diethyl ether and extracted three times with equal volumes of 2 normal hydrochloric acid and water, respectively. The mixture was dried over magnesium sulfate, filtered and the solvent removed by evaporation under reduced pressure. The desired cyano((6-phenoxy-2-pyridinyl)methyl)-2,2-dimethyl-3-cyclopropane carboxaldehyde product was recovered by distillation at 140° C. and 0.1 torr in a yield of 3.0 grams.

Workup

  1. additionwas added
  2. stirringStirring
  3. temperaturewas maintained for 15 minutes
  4. additionwas added
  5. stirringThe reaction mixture was stirred at room temperature for 24 hours
  6. filtrationAt the completion of this time, the reaction mixture was filtered
  7. customthe solvent was removed by evaporation under reduced pressure
  8. extractionextracted three times with equal volumes of 2 normal hydrochloric acid and water
  9. dry with materialThe mixture was dried over magnesium sulfate
  10. filtrationfiltered
  11. customthe solvent removed by evaporation under reduced pressure
  12. distillationThe desired cyano((6-phenoxy-2-pyridinyl)methyl)-2,2-dimethyl-3-cyclopropane carboxaldehyde product was recovered by distillation at 140° C.

Sources & evidence

ORD record
ord-38b2e2533585406b9b0b457ead481bb7
Source dataset
uspto-grants-1984_11
Patent number
US04485238

Reaction notes

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