p-Toluenesulfonic acid → HCID 1485818, compound

HRID 1494447Notes

Reaction equation

HRID 1494447 reaction equation
[F:1][C:2]1[CH:8]=[C:7]([F:9])[CH:6]=[CH:5][C:3]=1[NH2:4].[C:10]1(=O)[O:14][CH2:13][CH2:12][CH2:11]1.C1(C)C=CC(S(O)(=O)=O)=CC=1>O>[F:1][C:2]1[CH:8]=[C:7]([F:9])[CH:6]=[CH:5][C:3]=1[N:4]1[CH2:10][CH2:11][CH2:12][C:13]1=[O:14]

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 7302Gamma-ButyrolactoneHCID 97092,4-Difluoroaniline

Product 1

HCID 1485818HCID 1485818, compound

Reagents, catalysts & solvents 1

HCID 962WaterCatalyst

Conditions

Temperature
100 °C

Procedure

A mixture of 64.6 g of 2,4-difluoroaniline, 51.7 g of butyrolactone, 2 g of p-toluenesulphonic acid and a few drops of water is warmed to reflux (100 ° C.) with stirring. The water which forms is removed by distillation via a vigorous stream of nitrogen. During this operation, the internal temperature increases to 162° over the course of 15 hours. After cooling to room temperature, the mixture is diluted with 100 ml of diethyl ether. The ether solution is washed first with 5% strength HCl and then with 10% strength NaOH, dried and evaporated. The crystalline residue is recrystallized from ethanol. The 1-(2,4-difluorophenyl)pyrrolid-2-one obtained melts at 95°-97°.

Workup

  1. temperatureis warmed
  2. customThe water which forms is removed by distillation via a vigorous stream of nitrogen
  3. temperatureDuring this operation, the internal temperature increases to 162° over the course of 15 hours
  4. temperatureAfter cooling to room temperature
  5. additionthe mixture is diluted with 100 ml of diethyl ether
  6. washThe ether solution is washed first with 5% strength HCl
  7. dry with materialwith 10% strength NaOH, dried
  8. customevaporated
  9. customThe crystalline residue is recrystallized from ethanol

Sources & evidence

ORD record
ord-418fbb0f5d8c47a0814ff0ee052a68e6
Source dataset
uspto-grants-1991_06
Patent number
US05026625

Reaction notes

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