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

HRID 1418859Notes

Reaction equation

HRID 1418859 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 2N 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 2N 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-9f7b4d20dd1741f69fc08202b6c0172f
Source dataset
uspto-grants-1999_03
Patent number
US05885985

Reaction notes

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