Sodium Hydroxide → N-benzyl-3-oxo-2-(phenylhydrazinylidene)butanamide

HRID 2848

Reaction equation

HRID 2848 reaction equation
[CH2:1]([NH:8][C:9](=[O:14])[CH2:10][C:11](=[O:13])[CH3:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+].[Cl-].[C:18]1([N+:24]#[N:25])[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>O>[CH2:1]([NH:8][C:9](=[O:14])[C:10](=[N:25][NH:24][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[C:11](=[O:13])[CH3:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 60992Benzenediazonium chlorideHCID 70159Acetoacetobenzylamide

Product 1

HCID 178418323N-benzyl-3-oxo-2-(phenylhydrazinylidene)butanamide

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

7.27 g (0.038) of N-benzyl-3-oxobutyramide were dissolved in a solution of 5.32 g (0.133 mol) of NaOH in 58 ml of water. To the ice-cooled stirred solution, 0.040 mol of phenyldiazonium chloride were added dropwise at such a rate as to keep the temperature at 0° C. The precipitated solid was filtered and recrystallised from MeOH yielding 9 g of the title compound. M.p.=101°-103° C.

Workup

  1. additionwere added dropwise at such a rate as
  2. customat 0° C
  3. filtrationThe precipitated solid was filtered
  4. customrecrystallised from MeOH yielding 9 g of the title compound

Sources & evidence

ORD record
ord-24aef19954464872a4172777d7b361e8
Source dataset
uspto-grants-1998_03
Patent number
US05731322

Linked notes

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