p-Toluenesulfonic acid → HCID 53687538, compound

HRID 597096Notes

Reaction equation

HRID 597096 reaction equation
[F:1][C:2]([F:23])([F:22])[C:3]1[CH:4]=[C:5]([N:13]2[CH2:17][CH:16]([C:18]([OH:20])=[O:19])[CH2:15][C:14]2=[O:21])[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1.[C:24]1(C)C=CC(S(O)(=O)=O)=CC=1.C(=O)([O-])[O-].[Na+].[Na+]>CO>[CH3:24][O:19][C:18]([CH:16]1[CH2:17][N:13]([C:5]2[CH:6]=[C:7]([C:9]([F:11])([F:10])[F:12])[CH:8]=[C:3]([C:2]([F:22])([F:1])[F:23])[CH:4]=2)[C:14](=[O:21])[CH2:15]1)=[O:20]

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 10340Sodium CarbonateHCID 22051563HCID 22051563, compound

Product 1

HCID 53687538HCID 53687538, compoundYield 1,357.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
20 °C

Procedure

8.8 g (0.025 mole) of the 1-(3,5-bis-trifluoromethylphenyl)-2-oxo-pyrrolidine-4-carboxylic acid produced according to Example 1 is refluxed together with 0.3 g of p-toluenesulphonic acid in 130 ml of absolute methanol, and the reaction mixture is kept at this temperature during 17 hours. It is subsequently cooled to 20° C and 0.1 g of sodium carbonate is added. Excess methanol is evaporated off. The residue is dissolved in diethyl ether, extracted three times with water, dried, and concentrated by evaporation. By recrystallisation from n-hexane there is obtained 8.4 g (91% of theory) of 1-(3,5-bis-trifluoromethylphenyl)-2-oxo-pyrrolidine-4-carboxylic acid methyl ester; m.p. 68°-70° C. Analysis for C14H11F6NO3 (molar weight 355.17):

Workup

  1. customExcess methanol is evaporated off
  2. dissolutionThe residue is dissolved in diethyl ether
  3. extractionextracted three times with water
  4. customdried
  5. concentrationconcentrated by evaporation
  6. customBy recrystallisation from n-hexane

Sources & evidence

ORD record
ord-8629100345404bce95bda29b41467d1b
Source dataset
uspto-grants-1977_03
Patent number
US04013445

Reaction notes

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