Oxalic Acid → N-(2-fluorophenyl)-1-pyrrolidinecarboximidamide

HRID 609573Notes

Reaction equation

HRID 609573 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH:8][C:9](=[NH:12])SC.[NH:13]1[CH2:17][CH2:16][CH2:15][CH2:14]1.C(O)(=O)C(O)=O>C(O)C.C(O)(C)C>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH:8][C:9]([N:13]1[CH2:17][CH2:16][CH2:15][CH2:14]1)=[NH:12]

Participants

6

Reactant 3

HCID 971Oxalic AcidHCID 31268PyrrolidineHCID 178503973HCID 178503973, compound

Product 1

HCID 178511984N-(2-fluorophenyl)-1-pyrrolidinecarboximidamide

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 3776IsopropanolSolvent

Procedure

To stirred solution of 2.0 g (0.006 mol) of N-(2-fluorophenyl)-S-methylisothiourea in 50 ml of ethanol was added 2.0 g (0.028 mol) of pyrrolidine and the reaction refluxed for eight hours. The solvent was then evaporated and to the residue was added 100 ml of water and 20 ml of 2 N sodium hydroxide. The aqueous phase was then extracted with ethyl acetate (3×100 ml) and the organic phase dried over magnesium sulphate. Evaporation of the solvent gave a crude residue. This crude residue was then dissolved in 25 ml of hot isopropanol and oxalic acid was added in excess. Upon cooling a white solid crystallized and was collected by filtration and dried at 60° C. for 24 hours to give the oxalate salt of N-(2-fluorophenyl)-1-pyrrolidinecarboximidamide, M.P. 172-173° C.

Workup

  1. temperaturethe reaction refluxed for eight hours
  2. customThe solvent was then evaporated and to the residue
  3. additionwas added 100 ml of water and 20 ml of 2 N sodium hydroxide
  4. extractionThe aqueous phase was then extracted with ethyl acetate (3×100 ml)
  5. dry with materialthe organic phase dried over magnesium sulphate
  6. customEvaporation of the solvent
  7. customgave a crude residue
  8. temperatureUpon cooling a white solid
  9. customcrystallized
  10. filtrationwas collected by filtration
  11. customdried at 60° C. for 24 hours

Sources & evidence

ORD record
ord-aa64b4916f5045599c8b4b5410cc4492
Source dataset
uspto-grants-1999_12
Patent number
US05998399

Reaction notes

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