Pyrrolidine → N-(2-Phenylethenesulfonyl)pyrrolidine-1-carboxamide

HRID 2163688Notes

Reaction equation

HRID 2163688 reaction equation
ClC1C=[C:4]([NH:8][C:9]([NH:11][S:12]([CH:15]=[CH:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)(=[O:14])=[O:13])=[O:10])[CH:5]=[CH:6][CH:7]=1.N1CCCC1>C(O)C>[N:8]1([C:9]([NH:11][S:12]([CH:15]=[CH:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)(=[O:14])=[O:13])=[O:10])[CH2:4][CH2:5][CH2:6][CH2:7]1

Participants

4

Reactant 2

HCID 31268PyrrolidineHCID 54390905N-[(3-Chlorophenyl)carbamoyl]-2-phenylethene-1-sulfonamide

Product 1

HCID 53740931N-(2-Phenylethenesulfonyl)pyrrolidine-1-carboxamide

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 3.4 g. of N-(N-[m-chlorophenyl]carbamoyl)-2-phenylethenesulfonamide and 2.15 g. of pyrrolidine in 100 ml. of ethanol is heated under reflux for 20 hours. The solution is cooled, and then it is concentrated in vacuo to ca. 25 ml. A small amount of starting material precipitates and it is filtered off. To the ethanol filtrate is then added 75 ml. of ether and 75 ml. of water. The layers are separated, and the aqueous layer is acidified using concentrated hydrochloric acid. This causes the crude product to precipitate. It is filtered off, and when dry it weighs 1.5 g. The ether layer is washed with 50 ml. of 1N hydrochloric acid, followed by 25 ml. of water. After being dried using anhydrous sodium sulfate, the ether is evaporated in vacuo to give a second crop of product (0.70 g.). The first crop of product is recrystallized from acetone to 0.60 g. of pure-N-(pyrrolidinocarbonyl)-2-phenylethenesulfonamide, m.p. 201°-204° C.

Workup

  1. additionA mixture of 3.4 g
  2. temperatureunder reflux for 20 hours
  3. temperatureThe solution is cooled
  4. concentrationit is concentrated in vacuo to ca. 25 ml
  5. customA small amount of starting material precipitates
  6. filtrationit is filtered off
  7. additionTo the ethanol filtrate is then added 75 ml
  8. customThe layers are separated
  9. customto precipitate
  10. filtrationIt is filtered off
  11. customwhen dry it
  12. washThe ether layer is washed with 50 ml
  13. customAfter being dried
  14. customthe ether is evaporated in vacuo
  15. customto give a second crop of product (0.70 g.)
  16. customThe first crop of product is recrystallized from acetone to 0.60 g

Sources & evidence

ORD record
ord-b3494f9363f04816b7f65667e90afe3e
Source dataset
uspto-grants-1979_01
Patent number
US04136180

Reaction notes

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