Benzylamine → 3-(5-Benzylamino-3-bromo-4-nitropyrazol-1-yl)propan-1-ol

HRID 1181153Notes

Reaction equation

HRID 1181153 reaction equation
[Br:1][C:2]1[C:6]([N+:7]([O-:9])=[O:8])=[C:5](Br)[N:4]([CH2:11][CH2:12][CH2:13][OH:14])[N:3]=1.[CH2:15]([NH2:22])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>CCO>[CH2:15]([NH:22][C:5]1[N:4]([CH2:11][CH2:12][CH2:13][OH:14])[N:3]=[C:2]([Br:1])[C:6]=1[N+:7]([O-:9])=[O:8])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

4

Reactant 2

HCID 7504BenzylamineHCID 231041703-(3,5-Dibromo-4-nitropyrazol-1-yl)propan-1-ol

Product 1

HCID 130072283-(5-Benzylamino-3-bromo-4-nitropyrazol-1-yl)propan-1-ol

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 3-(3,5-dibromo-4-nitropyrazol-1-yl)propan-1-ol (3-2) (17.1 g, 52 mmol), EtOH (100 ml) and benzylamine (27.9 g, 260 mmol) was refluxed for 15 hours. The reaction medium was concentrated to the maximum under reduced pressure. The highly viscous residue was suspended in EtOAc (100 ml) and EtOH (100 ml). The organic phase was washed with NaCl solution (10%, 100 ml) and then dried over Na2SO4. After evaporating off the solvent under reduced pressure, an orange-colored oil was obtained (13.6 g), which was subsequently purified by column chromatography (gradient: 10%/90% EtOAc/hexane to 40%/60% EtOAc/hexane) in order to obtain, after evaporating off the solvent, the 3-(5-benzylamino-3-bromo-4-nitropyrazol-1-yl)propan-1-ol in the form of a yellow solid (8.8 g, 48%).

Workup

  1. temperaturewas refluxed for 15 hours
  2. concentrationThe reaction medium was concentrated to the maximum under reduced pressure
  3. washThe organic phase was washed with NaCl solution (10%, 100 ml)
  4. dry with materialdried over Na2SO4
  5. customAfter evaporating off the solvent under reduced pressure
  6. customan orange-colored oil was obtained (13.6 g), which
  7. customwas subsequently purified by column chromatography (gradient: 10%/90% EtOAc/hexane to 40%/60% EtOAc/hexane) in order
  8. customto obtain
  9. customafter evaporating off the solvent

Sources & evidence

ORD record
ord-4e7d778970bb47008148702d2a8cb166
Source dataset
uspto-grants-2007_10
Patent number
US07285136B2

Reaction notes

Loading…