Benzyl Bromide → N'-t-butyl-N-benzoyl-N'-benzylhydrazine

HRID 849789Notes

Reaction equation

HRID 849789 reaction equation
[CH2:1](Br)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:9]([NH:17][NH:18][C:19]([CH3:22])([CH3:21])[CH3:20])(=[O:16])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.C(N(CC)CC)C>CN(C)C=O.C(OCC)C>[C:19]([N:18]([CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[NH:17][C:9](=[O:16])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)([CH3:22])([CH3:21])[CH3:20]

Participants

6

Reactant 3

HCID 7498Benzyl BromideHCID 8471TriethylamineHCID 299436N'-tert-butylbenzohydrazide

Product 1

HCID 15452008N'-t-butyl-N-benzoyl-N'-benzylhydrazine

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Procedure

Benzyl bromide (0.9 g), 1-benzoyl-2-t-butyl hydrazine (1 g) and triethylamine (0.52 g) were warmed in dimethylformamide (50 ml) at 50° C. for 2 hours. The reaction mixture was cooled to room temperature, diluted with diethylether (100 ml) and washed three times with 25 ml of water. The organic layer was dried over magnesium sulfate, filtered, and the solvent removed in vacuo to afford the product as a white solid. The product was chromatographed on silica gel (G:70 to 230 mesh) using methylene chloride as eluent to afford a 75% yield of a white solid: m.p. 147-149.

Workup

  1. washwashed three times with 25 ml of water
  2. dry with materialThe organic layer was dried over magnesium sulfate
  3. filtrationfiltered
  4. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-01d9f77e2c174fe597edb23e303d734f
Source dataset
uspto-grants-2000_01
Patent number
US06013836

Reaction notes

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