Pyrazole-1-carboxamidine monohydrochloride → N-[1-(4-nitrophenyl)pyrrolidin-3-yl]guanidine

HRID 496529Notes

Reaction equation

HRID 496529 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([N:10]2[CH2:14][CH:13]([NH2:15])[CH2:12][CH2:11]2)=[CH:6][CH:5]=1)([O-:3])=[O:2].Cl.[C:17](N1C=CC=N1)(=[NH:19])[NH2:18]>CN(C=O)C>[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([N:10]2[CH2:11][CH2:12][CH:13]([NH:15][C:17]([NH2:19])=[NH:18])[CH2:14]2)=[CH:6][CH:5]=1)([O-:3])=[O:2]

Participants

4

Reactant 2

HCID 2734672Pyrazole-1-carboxamidine monohydrochlorideHCID 120678271-(4-Nitrophenyl)pyrrolidin-3-ylamine

Product 1

HCID 178512585N-[1-(4-nitrophenyl)pyrrolidin-3-yl]guanidineYield 891.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2.07 g (0.01 mol) of [1-(4-nitrophenyl)pyrrolidin-3-yl]amine (2) was heated to 90° C. in 10 ml of DMF. 1.32 g (0.0009 mol) of 1-amidinopyrazole monohydrochloride was added slowly to the reaction medium. The mixture was heated for 8 hours. A yellow solid was thus precipitated. The solid thus obtained was filtered off, washed with ethanol and dried under vacuum to give 2 g of a yellow powder (3) (70%).

Workup

  1. temperatureThe mixture was heated for 8 hours
  2. customA yellow solid was thus precipitated
  3. customThe solid thus obtained
  4. filtrationwas filtered off
  5. washwashed with ethanol
  6. customdried under vacuum

Sources & evidence

ORD record
ord-c0938aa66dc24964a466305d8c8d3771
Source dataset
uspto-grants-2005_09
Patent number
US06946005B2

Reaction notes

Loading…