p-Toluenesulfonic acid → [1-(2-Oxo-1-pyrrolidinyl)ethyl]tolyltriazole

HRID 487836Notes

Reaction equation

HRID 487836 reaction equation
[C:1]1([CH3:12])[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]1[N:8]=[N:9][NH:10][CH:11]=1.[CH:13]([N:15]1[CH2:19][CH2:18][CH2:17][C:16]1=[O:20])=[CH2:14].C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[O:20]=[C:16]1[CH2:17][CH2:18][CH2:19][N:15]1[CH:13]([C:11]1[NH:10][N:9]=[N:8][C:7]=1[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][C:1]=1[CH3:12])[CH3:14]

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 6917N-vinyl-2-pyrrolidoneHCID 178424185HCID 178424185, compound

Product 1

HCID 178424212[1-(2-Oxo-1-pyrrolidinyl)ethyl]tolyltriazole

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of tolyltriazole (26.6 g; 0.2 moles), 1-vinyl-2-pyrrolidinone (22.2 g; 0.2 moles) and para toluene sulphonic acid (0.14 g) is heated in toluene (200 ml), under reflux, for 7 hours. The mixture is then cooled to ambient temperature and washed with 5% sodium bicarbonate solution (50 ml), water (2×50 ml) and finally, dried over anhydrous magnesium sulphate. The dried extract is filtered and then evaporated to yield a yellow oil. Short-path distillation of the crude product yields a pale yellow viscous oil (34.9 g; 71%), bp 175°/0.05 mbar.

Workup

  1. temperatureunder reflux, for 7 hours
  2. washwashed with 5% sodium bicarbonate solution (50 ml), water (2×50 ml)
  3. dry with materialfinally, dried over anhydrous magnesium sulphate
  4. extractionThe dried extract
  5. filtrationis filtered
  6. customevaporated
  7. customto yield a yellow oil
  8. distillationShort-path distillation of the crude product
  9. customyields a pale yellow viscous oil (34.9 g; 71%), bp 175°/0.05 mbar

Sources & evidence

ORD record
ord-cfd2adac19674dc9a38f56f5a35d9ced
Source dataset
uspto-grants-1994_03
Patent number
US05298178

Reaction notes

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