Toluene → [1-(2-Oxo-1-pyrrolidinyl)ethyl]tolyltriazole

HRID 654647Notes

Reaction equation

HRID 654647 reaction equation
[CH3:1][C:2]1[C:10]2[C:6](=[N:7][NH:8][N:9]=2)[CH:5]=[CH:4][CH:3]=1.C([N:13]1[CH2:17][CH2:16][CH2:15][C:14]1=[O:18])=C.[C:19]1(C)[CH:24]=CC(S(O)(=O)=O)=C[CH:20]=1.[C:30]1(C)C=CC=CC=1>>[O:18]=[C:14]1[CH2:15][CH2:16][CH2:17][N:13]1[CH:5]([C:6]1[NH:7][N:8]=[N:9][C:10]=1[C:2]1[CH:3]=[CH:24][CH:19]=[CH:20][C:1]=1[CH3:30])[CH3:4]

Participants

5

Reactant 4

HCID 1140TolueneHCID 6101p-Toluenesulfonic acidHCID 6917N-vinyl-2-pyrrolidoneHCID 1224994-Methyl-1H-benzotriazole

Product 1

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

Procedure

A mixture of tolytriazole (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-e701ec00a8c64f8292ae06f8fe4b59e9
Source dataset
uspto-grants-1992_07
Patent number
US05133890

Reaction notes

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