Gamma-Butyrolactone → HCID 701787, compound

HRID 1390279Notes

Reaction equation

HRID 1390279 reaction equation
[F:1][C:2]([F:11])([F:10])[C:3]1[CH:4]=[C:5]([CH:7]=[CH:8][CH:9]=1)[NH2:6].[C:12]1(=O)[O:16][CH2:15][CH2:14][CH2:13]1.C1(C)C=C(C)C=C(C)C=1>O>[F:1][C:2]([F:10])([F:11])[C:3]1[CH:4]=[C:5]([N:6]2[CH2:12][CH2:13][CH2:14][C:15]2=[O:16])[CH:7]=[CH:8][CH:9]=1

Participants

5

Reactant 3

HCID 7302Gamma-ButyrolactoneHCID 73753-(Trifluoromethyl)anilineHCID 7947Mesitylene

Product 1

HCID 701787HCID 701787, compoundYield 45.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
198 °C

Procedure

A reaction flask was charged with 70.0 g (0.434 mole) of m-trifluoromethylaniline and 37.4 g (0.434 mole) of butyrolactone. The mixture was heated to reflux at 198° C for 185 minutes. Then, 1.0 g (0.0058 mole) of ptoluenesulphonic acid was added, and the resulting mixture was refluxed for an additional 100 minutes, during which time the temperature dropped from 164° C to 138° C. The mixture was then cooled, a DEan-Stark trap was installed on the condenser, and 50 ml of mesitylene was added. The mixture was then refluxed at 181-187° C until water was no longer produced. The precipitate formed by the reaction was filtered out of the mixture and dried in vacuo, yielding 45.6 g of 1-(m-trifluoromethylphenyl)-2-pyrrolidone, melting point 65°-66° C.

Workup

  1. temperatureThe mixture was heated
  2. temperaturethe resulting mixture was refluxed for an additional 100 minutes, during which time the temperature
  3. additiondropped from 164° C to 138° C
  4. temperatureThe mixture was then cooled
  5. additionwas added
  6. customno longer produced
  7. customThe precipitate formed by the reaction
  8. filtrationwas filtered out of the mixture
  9. customdried in vacuo

Sources & evidence

ORD record
ord-69b3d1e636fc48abad50090ca1f0b027
Source dataset
uspto-grants-1979_02
Patent number
US04138495

Reaction notes

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