Propargyl bromide → N-(2-propynyl)-N'-(3,5-dimethylbenzoyl)hydrazine

HRID 21631Notes

Reaction equation

HRID 21631 reaction equation
C([N:5]([C:15](=[O:24])[C:16]1[CH:21]=[C:20]([CH3:22])[CH:19]=[C:18]([CH3:23])[CH:17]=1)[NH:6][C:7](=O)[C:8]1C=CC=C[CH:9]=1)(C)(C)C.[H-].[Na+].C(Br)C#C>CN(C)C=O.C(OCC)(=O)C>[CH2:7]([NH:6][NH:5][C:15](=[O:24])[C:16]1[CH:17]=[C:18]([CH3:23])[CH:19]=[C:20]([CH3:22])[CH:21]=1)[C:8]#[CH:9]

Participants

6

Reactant 3

HCID 7842Propargyl bromideHCID 24758Sodium hydrideHCID 183463N'-benzoyl-N-tert-butyl-3,5-dimethylbenzohydrazide

Product 1

HCID 19933223N-(2-propynyl)-N'-(3,5-dimethylbenzoyl)hydrazineYield 70%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a stirred suspension of N'-t-butyl-N-benzoyl-N'-(3,5-dimethylbenzoyl)hydrazine (1.5 g) in dimethylformamide (DMF) (20 ml) was added sodium hydride (200 mg of 60% oil dispersion) portionwise. After 15 min., propargyl bromide (0.6 g) was added to the reaction mixture dropwise and the reaction stirred for 1 hour. The reaction mixture was diluted with ethyl acetate (50 ml) and washed with water (5×20 ml). The organic layer was then dried over magnesium sulfate and the solvent removed under vacuum to afford N-(2-propynyl)-N'-(3,5-dimethylbenzoyl)hydrazine as a yellow amorphous solid. The product, N-(2-propynyl)-N'-t-butyl-N-benzoyl-N'-(3,5-dimethylbenzoyl)hydrazine, was purified by column chromatography on silica gel (solvent system: methylene chloride) to afford a 70% yield as a white solid.

Workup

  1. washwashed with water (5×20 ml)
  2. dry with materialThe organic layer was then dried over magnesium sulfate
  3. customthe solvent removed under vacuum

Sources & evidence

ORD record
ord-44b885771ce240ba9a2a4693113c016c
Source dataset
uspto-grants-1995_06
Patent number
US05424333

Reaction notes

Loading…