Benzylamine → HCID 13007231, compound

HRID 1181156Notes

Reaction equation

HRID 1181156 reaction equation
[Br:1][C:2]1[C:6]([N+:7]([O-:9])=[O:8])=[C:5](Br)[N:4]([CH:11](O)[CH:12]([OH:14])[CH3:13])[N:3]=1.[CH2:16]([NH2:23])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.C([O:27]C(C)C)(C)C>CCO>[CH2:16]([NH:23][C:5]1[N:4]([CH2:11][CH:12]([OH:14])[CH2:13][OH:27])[N:3]=[C:2]([Br:1])[C:6]=1[N+:7]([O-:9])=[O:8])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

5

Reactant 3

HCID 7504BenzylamineHCID 7914Diisopropyl EtherHCID 69424420HCID 69424420, compound

Product 1

HCID 13007231HCID 13007231, compoundYield 42%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 1-(3,5-dibromo-4-nitropyrazol-1-yl)-propane-1,2-diol (3-4) (31 g, 898 mmol), EtOH (420 ml) and benzylamine (138 g, 1.26 mol) was refluxed for 1.5 hours. The reaction medium was concentrated to the maximum under reduced pressure. 100 ml of DCM were added to the residue. The organic phase was washed with dilute acid (5×50 ml). The organic phase was dried over Na2SO4 and the solvent was evaporated off under reduced pressure. The brown oil obtained was treated with diisopropyl ether at 0° C. to give the 3-(5-benzylamino-3-bromo-4-nitropyrazol-1-yl)propane-1,2-diol (14.1 g, 42%) in the form of a yellow solid.

Workup

  1. temperaturewas refluxed for 1.5 hours
  2. concentrationThe reaction medium was concentrated to the maximum under reduced pressure
  3. addition100 ml of DCM were added to the residue
  4. washThe organic phase was washed
  5. additionwith dilute acid (5×50 ml)
  6. dry with materialThe organic phase was dried over Na2SO4
  7. customthe solvent was evaporated off under reduced pressure
  8. customThe brown oil obtained

Sources & evidence

ORD record
ord-535201fe3cc143289faa4a4d75cb0b39
Source dataset
uspto-grants-2007_10
Patent number
US07285136B2

Reaction notes

Loading…