3,5-Dimethyl-1H-pyrazole-1-carboxamidine mononitrate → HCID 178512768, compound

HRID 1731489Notes

Reaction equation

HRID 1731489 reaction equation
[I:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[NH2:10])[CH2:5][NH2:6].[N+]([O-])(O)=O.CC1C=C(C)[N:18]([C:22](N)=[NH:23])N=1>C(O)C>[I:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[NH2:10])[CH2:5][NH:6][C:22]([NH2:23])=[NH:18]

Participants

4

Reactant 2

HCID 1981863,5-Dimethyl-1H-pyrazole-1-carboxamidine mononitrateHCID 103546234-(aminomethyl)-2-iodoaniline

Product 1

HCID 178512768HCID 178512768, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

An ethanol (5 ml) solution of 3-iodo-4-aminobenzylamine (0.220 g, 0.887 mmol) and 3,5-dimethylpyrazole-1-carboxamidine nitrate (0.179 g, 0.087 mmol) was heated at reflux temperature for 3 hr. under argon. The solvent was evaporated in vacuo and the residue washed with ether and dichloromethane to remove 3,5-dimethylpyrazole and unreacted amine. The crude product was recrystallized from methanol/ether to give fine, pale-yellow needles (0.163 g, 72.5%), mp 135°-137° C.; PMR (DMSO-d6) γ6.62-7.66 (m, 9H), 4.1 (s, 2H); IR (Nujol) 1660, 1620 cm-1 (C=N); Anal. Calcd. for C18H11IN4. HNO3.0.5H2O): C, 27.20; H, 3.42, N, 19.08. Found C, 26.70; H, 3.33; N, 19.08.

Workup

  1. temperatureat reflux temperature for 3 hr
  2. customThe solvent was evaporated in vacuo
  3. washthe residue washed with ether and dichloromethane
  4. customto remove 3,5-dimethylpyrazole and unreacted amine
  5. customThe crude product was recrystallized from methanol/ether
  6. customto give fine

Sources & evidence

ORD record
ord-bd933e877c054d4b977bf8030efeafea
Source dataset
uspto-grants-1986_11
Patent number
US04622217

Reaction notes

Loading…