Potassium Carbonate → N-benzoyl-N'-t-butyl-N'-(ethoxycarbonyl)methylhydrazine

HRID 1197290Notes

Reaction equation

HRID 1197290 reaction equation
[C:1]([NH:5][NH:6][C:7](=[O:14])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)([CH3:4])([CH3:3])[CH3:2].C(=O)([O-])[O-].[K+].[K+].[C:21]([O:24][CH2:25][CH2:26]Br)(=[O:23])[CH3:22]>CN(C)C=O.O.CCOCC>[C:7]([NH:6][N:5]([C:1]([CH3:4])([CH3:2])[CH3:3])[CH2:22][C:21]([O:24][CH2:25][CH3:26])=[O:23])(=[O:14])[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 135641-Acetoxy-2-bromoethaneHCID 299436N'-tert-butylbenzohydrazide

Product 1

HCID 15452013N-benzoyl-N'-t-butyl-N'-(ethoxycarbonyl)methylhydrazineYield 9.4%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

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 rotavaped to afford an oil. Chromatographic purification gave the pure oil product (0.25 g).

Workup

  1. customthe organic layer was separated
  2. washThe organic layer was washed several times with water
  3. dry with materialdried over magnesium sulfate
  4. customto afford an oil
  5. customChromatographic purification

Sources & evidence

ORD record
ord-1c7ef194790643c2a6686f067d7bd61e
Source dataset
uspto-grants-1992_05
Patent number
US05117057

Reaction notes

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