Acetic Acid → HCID 57899332, compound

HRID 425752Notes

Reaction equation

HRID 425752 reaction equation
C(O)(=O)C.[Cl:5][C:6]1[CH:7]=[C:8]([CH2:13][NH:14][O:15][CH3:16])[CH:9]=[N:10][C:11]=1[Cl:12].[CH2:17]1[C:22](=[O:23])[O:21][CH2:20][C:18]1=O.O>C1(C)C=CC=CC=1>[Cl:5][C:6]1[CH:7]=[C:8]([CH2:13][N:14]([O:15][CH3:16])[C:18]2[CH2:20][O:21][C:22](=[O:23])[CH:17]=2)[CH:9]=[N:10][C:11]=1[Cl:12]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 962WaterHCID 521261Tetronic acidHCID 86634699HCID 86634699, compound

Product 1

HCID 57899332HCID 57899332, compoundYield 61%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

120 μl (2.04 mmol) of acetic acid and 422 mg (2.04 mmol) of 1-(5,6-dichloropyridin-3-yl)-N-methoxymethanamine (III-3) are added to 224 mg (2.24 mmol) of tetronic acid in 50 ml of toluene, and the mixture is heated under reflux on a water separator for 3 hours. The reaction mixture is concentrated under reduced pressure, the residue is taken up in ethyl acetate and the mixture is washed successively twice with 1 N aqueous hydrochloric acid, twice with 1 N aqueous sodium hydroxide solution and saturated sodium chloride solution and dried over sodium sulphate. Concentration of the organic phase under reduced pressure and purification of the residue by recrystallization from ethyl acetate gives 360 mg (59% of theory) of 4-[[(5,6-dichloropyridin-3-yl)methyl](methoxy)amino]furan-2(5H)-one.

Workup

  1. temperaturethe mixture is heated
  2. concentrationThe reaction mixture is concentrated under reduced pressure
  3. washthe mixture is washed successively twice with 1 N aqueous hydrochloric acid, twice with 1 N aqueous sodium hydroxide solution and saturated sodium chloride solution
  4. dry with materialdried over sodium sulphate
  5. customConcentration of the organic phase under reduced pressure and purification of the residue
  6. customby recrystallization from ethyl acetate

Sources & evidence

ORD record
ord-a644ee787ca945bab2c06e9a73ce27ee
Source dataset
uspto-grants-2012_01
Patent number
US08106212B2

Reaction notes

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