Reaction #49941

ord-037e49102d464965acd586fc010b4458

Reaction equation

CC(C)(C)NNC(=O)c1ccccc1
N'-t-butyl-N-benzoylhydrazine
O=C([O-])[O-].[K+].[K+]
potassium carbonate
CC(=O)OCCBr
bromoethyl acetate
→
CCOC(=O)CN(NC(=O)c1ccccc1)C(C)(C)C
product
Yield 9.4%
CCOC(=O)CN(NC(=O)c1ccccc1)C(C)(C)C
N-benzoyl-N'-t-butyl-N'-(ethoxycarbonyl)methylhydrazine
Yield 9.4%

Reactants

CC(C)(C)NNC(=O)c1ccccc1
N'-t-butyl-N-benzoylhydrazine
O=C([O-])[O-].[K+].[K+]
potassium carbonate
CC(=O)OCCBr
bromoethyl acetate

Reagents

None

Solvents

O
water
CCOCC
ether
CN(C)C=O
dimethylformamide

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    Otherthe organic layer was separated
  2. 2
    WashThe organic layer was washed several times with water
  3. 3
    Dryingdried over magnesium sulfate
  4. 4
    Otherto afford an oil
  5. 5
    OtherChromatographic purification

Procedure

N'-t-butyl-N-benzoylhydrazine (2.0 g), powdered potassium carbonate (5 g) and bromoethyl acetate (1.6 g) were stirred in dimethylformamide (20 ml) at 60° C. for 14 hours. The reaction mixture was diluted with water and ether, and the organic layer was separated. The organic layer was washed several times with water, dried over magnesium sulfate and rotavapped to afford an oil. Chromatographic purification gave the pure oil product (0.25 g).

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US05424333uspto-grants-1995_06