Sodium Bicarbonate → 2-tert-Butyl-4H-1,3,4-oxadiazin-5(6H)-one

HRID 877154

Reaction equation

HRID 877154 reaction equation
Cl[CH2:2][C:3]([NH:5][NH:6][C:7](=[O:12])[C:8]([CH3:11])([CH3:10])[CH3:9])=[O:4].C(=O)(O)[O-].[Na+]>CN(C=O)C>[C:8]([C:7]1[O:12][CH2:2][C:3](=[O:4])[NH:5][N:6]=1)([CH3:11])([CH3:10])[CH3:9]

Participants

4

Reactant 2

HCID 516892Sodium BicarbonateHCID 54595759N'-(2-chloroacetyl)-2,2-dimethylpropanehydrazide

Product 1

HCID 581363442-tert-Butyl-4H-1,3,4-oxadiazin-5(6H)-one

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

8.34 g (43.29 mmol) of N′-(chloroacetyl)-2,2-dimethylpropanehydrazide were dissolved in 800 ml of dry DMF, and 4.24 g (50.52 mmol) of sodium bicarbonate were added. The reaction mixture was heated at 100° C. overnight. After cooling, the solvent was removed on a rotary evaporator, water was added to the residue and the mixture was acidified with 1 N hydrochloric acid. The mixture was extracted three times with ethyl acetate, and the combined organic phases were washed with water, dried over sodium sulfate and concentrated on a rotary evaporator. This gave 5.05 g of the target compound. The crude product was reacted further without further purification.

Workup

  1. temperatureAfter cooling
  2. customthe solvent was removed on a rotary evaporator, water
  3. additionwas added to the residue
  4. extractionThe mixture was extracted three times with ethyl acetate
  5. washthe combined organic phases were washed with water
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated on a rotary evaporator
  8. customThe crude product was reacted further without further purification

Sources & evidence

ORD record
ord-271d273421ed4362b541e84fdde0b38c
Source dataset
uspto-grants-2015_03
Patent number
US08987256B2

Linked notes

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