Acetic Acid → HCID 69332645, compound

HRID 915008Notes

Reaction equation

HRID 915008 reaction equation
[CH:1]([N:4]1[C:9](=[O:10])[CH:8]=[CH:7][C:6]([CH:11]([NH:20][C:21](=[O:24])[O:22]C)[C:12](=O)[C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[N:5]1)([CH3:3])[CH3:2].[H-].[Na+].CC(O)=O.O>CN(C=O)C>[CH:1]([N:4]1[C:9](=[O:10])[CH:8]=[CH:7][C:6]([C:11]2[NH:20][C:21](=[O:22])[O:24][C:12]=2[C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[N:5]1)([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 962WaterHCID 24758Sodium hydrideHCID 86600904Methyl [1-(1-isopropyl-6-oxo-1,6-dihydro-3-pyridazinyl)-2-oxo-2-phenylethyl]carbamate

Product 1

HCID 69332645HCID 69332645, compoundYield 70.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
72.5 °C

Procedure

A solution of methyl [1-(1-isopropyl-6-oxo-1,6-dihydro-3-pyridazinyl)-2-oxo-2-phenylethyl]carbamate (2.46 g) in DMF (10 ml) was added to a suspension of NaH (60% dispersion in mineral oil) (314 mg) in DMF (15 ml) and the mixture was heated at 70-75° C. for 3 hours. A mixture of AcOH (0.5 ml) and water (75 ml) was added to the mixture to give a precipitate. The precipitate was collected by filtration and dried under reduced pressure to give 2-isopropyl-6-(2-oxo-5-phenyl-2,3-dihydro-oxazol-4-yl)-3(2H)-pyridazinone as a solid (1.56 g).

Workup

  1. additionwas added to the mixture
  2. customto give a precipitate
  3. filtrationThe precipitate was collected by filtration
  4. customdried under reduced pressure

Sources & evidence

ORD record
ord-fb990572489b4d6aaaec89f9b908d543
Source dataset
uspto-grants-2007_09
Patent number
US07265120B2

Reaction notes

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