Phenylhydrazine → HCID 14860705, compound

HRID 2256002Notes

Reaction equation

HRID 2256002 reaction equation
[C:1]([NH:4][CH:5](OCC)[C:6]([NH:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)=[O:7])(=[O:3])[CH3:2].B(Br)(Br)Br.[C:23]1([NH:29][NH2:30])[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>>[C:1]([NH:4][CH:5]([NH:30][NH:29][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[C:6]([NH:8][CH2:9][C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1)=[O:7])(=[O:3])[CH3:2]

Participants

4

Reactant 3

HCID 7516PhenylhydrazineHCID 25134Boron tribromideHCID 14212862HCID 14212862, compound

Product 1

HCID 14860705HCID 14860705, compound

Procedure

Using 2-acetamido-N-benzyl-2-ethoxyacetamide (2.00 g, 8.0 mmol), BBr3 (1M in CH2Cl2, 10.0 mL, 10.0 mmol), and phenylhydrazine (2.60 g, 24.0 mmol) gave a pale yellow oily residue which was purified by flash column chromatography on SiO2 gel (2% MeOH/CHCl3) to give the desired product. The product was recrystallized from chloroform/hexane as a light yellow solid.

Workup

  1. customgave a pale yellow oily residue which
  2. customwas purified by flash column chromatography on SiO2 gel (2% MeOH/CHCl3)

Sources & evidence

ORD record
ord-57819b627c704b0587475ae5ad70c6a2
Source dataset
uspto-grants-1997_08
Patent number
US05654301

Reaction notes

Loading…