Ethyl Acetate → HCID 57927460, compound

HRID 889154Notes

Reaction equation

HRID 889154 reaction equation
[O:1]1[CH:5]=[C:4]([C:6]([NH:8][NH2:9])=[O:7])[N:3]=[CH:2]1.CCCCCCC.[C:17](OCC)(=[O:19])C>ClC(OC(Cl)(Cl)Cl)=O>[O:1]1[CH:5]=[C:4]([C:6]2[O:7][C:17](=[O:19])[NH:9][N:8]=2)[N:3]=[CH:2]1

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 8900HeptaneHCID 497617151,3-Oxazole-4-carbohydrazide

Product 1

HCID 57927460HCID 57927460, compound

Reagents, catalysts & solvents 1

HCID 10426DiphosgeneSolvent

Procedure

After suspending oxazole-4-carboxylic acid hydrazide (CAS 885274-12-4) (1.06 g) in ethyl acetate (10 ml), trichloromethyl chloroformate (1.21 ml) was added dropwise while stirring on ice. Upon completion of the dropwise addition, the mixture was heated to reflux for 2 hours and 20 minutes. It was then allowed to cool, n-heptane was added to the reaction mixture, and the precipitate was collected by filtration. The filtrate was concentrated under reduced pressure and the residue was recrystallized with toluene-ethyl acetate. This was combined with the previously filtered substance to obtain the title compound (1.38 g).

Workup

  1. additionwas added dropwise
  2. additionUpon completion of the dropwise addition
  3. temperaturethe mixture was heated
  4. temperatureto reflux for 2 hours and 20 minutes
  5. temperatureto cool
  6. filtrationthe precipitate was collected by filtration
  7. concentrationThe filtrate was concentrated under reduced pressure
  8. customthe residue was recrystallized with toluene-ethyl acetate

Sources & evidence

ORD record
ord-f410baf8e0504ce09ec5f5587acf8550
Source dataset
uspto-grants-2012_08
Patent number
US08252810B2

Reaction notes

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