Ethyl Acetate → HCID 178512008, compound

HRID 1418853Notes

Reaction equation

HRID 1418853 reaction equation
Cl.[C:2]1([NH:8][C:9]([CH2:11][CH2:12][CH2:13][C:14]2[CH:20]=[CH:19][C:17]([NH2:18])=[CH:16][CH:15]=2)=[O:10])[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[N:21]1([C:26]#[N:27])[CH2:25][CH2:24][CH2:23][CH2:22]1.C(OCC)(=O)C>ClC1C=CC=CC=1.CN(C)C1C=CN=CC=1.C(O)(C)C>[C:2]1([NH:8][C:9]([CH2:11][CH2:12][CH2:13][C:14]2[CH:20]=[CH:19][C:17]([NH:18][C:26]([N:21]3[CH2:25][CH2:24][CH2:23][CH2:22]3)=[NH:27])=[CH:16][CH:15]=2)=[O:10])[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 3

HCID 8857Ethyl AcetateHCID 73737Pyrrolidine-1-carbonitrileHCID 19599218HCID 19599218, compound

Product 1

HCID 178512008HCID 178512008, compound

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 3776IsopropanolSolventHCID 7964ChlorobenzeneSolvent

Procedure

To a stirred suspension of the product of step (a) (1.7 g; 0.0052 moles) in 30 ml of chlorobenzene was added a catalytic amount of 4-dimethylaminopyridine. To this was added 1-pyrrolidinecarbonitrile (1.2 ml; 0.016 moles) and the reaction then heated to reflux for 6 hours. The reaction was then cooled and the solvent decanted. To the residue was added 100 ml of 2N sodium hydroxide. The aqueous phase was then extracted 3×75 ml of chloroform and the organic extract was dried over magnesium sulphate. Evaporation of the solvent gave a white solid which was the dissolved in hot isopropanol 5 ml, and 100 ml ethyl acetate. Upon cooling a white solid crystallized and was collected by filtration. The above compound was dried at 70° C. for 72 hours to give N-(4(3-((phenylamino)carbonyl)propyl)phenyl)-1-pyrrolidinecarboximidamide, M.P.164°-165° C.

Workup

  1. customthe reaction
  2. temperaturethen heated
  3. temperatureto reflux for 6 hours
  4. temperatureThe reaction was then cooled
  5. customthe solvent decanted
  6. additionTo the residue was added 100 ml of 2N sodium hydroxide
  7. extractionThe aqueous phase was then extracted 3×75 ml of chloroform
  8. extractionthe organic extract
  9. dry with materialwas dried over magnesium sulphate
  10. customEvaporation of the solvent
  11. customgave a white solid which
  12. temperatureUpon cooling a white solid
  13. customcrystallized
  14. filtrationwas collected by filtration
  15. customThe above compound was dried at 70° C. for 72 hours

Sources & evidence

ORD record
ord-13b545ee9d6746029453bf78540ee79a
Source dataset
uspto-grants-1999_03
Patent number
US05885985

Reaction notes

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