Dimethylformamide → Pyrazinecarboxylic acid, (2,2-dimethyl-1-oxopropoxy)methyl ester

HRID 1440018Notes

Reaction equation

HRID 1440018 reaction equation
[N:1]1[CH:6]=[CH:5][N:4]=[CH:3][C:2]=1[C:7]([O-:9])=[O:8].[Na+].[C:11]([O:17][CH2:18]Cl)(=[O:16])[C:12]([CH3:15])([CH3:14])[CH3:13].CN(C)C=O>C1(C)C=CC=CC=1>[N:1]1[CH:6]=[CH:5][N:4]=[CH:3][C:2]=1[C:7]([O:9][CH2:18][O:17][C:11](=[O:16])[C:12]([CH3:15])([CH3:14])[CH3:13])=[O:8]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 87885Chloromethyl pivalateHCID 23709643HCID 23709643, compound

Product 1

HCID 10331752Pyrazinecarboxylic acid, (2,2-dimethyl-1-oxopropoxy)methyl esterYield 78%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A four-necked flask was charged with 127.5 g (0.873 mole) of sodium pyrazinecarboxylate, 119.3 g (0.792 mole) of chloromethyl pivalate and 146 g of dimethylformamide and the internal temperature was maintained under stirring at 105°-110° C. for 8 hours. The reaction mixture was then cooled and transferred to a separatory funnel. After addition of 500 g of toluene, the mixture was washed with 3 portions, or a total of 900 g, of water. From the toluene layer which separated the toluene was first distilled off and the residue was subjected to distillation under reduced pressure to give 147 g of pivaloyloxymethyl pyrazinecarboxylate. Yield: 78% (based on chloromethyl pivalate).

Workup

  1. temperaturethe internal temperature was maintained
  2. temperatureThe reaction mixture was then cooled
  3. customtransferred to a separatory funnel
  4. washthe mixture was washed with 3 portions
  5. customFrom the toluene layer which separated the toluene
  6. distillationwas first distilled off
  7. distillationthe residue was subjected to distillation under reduced pressure

Sources & evidence

ORD record
ord-a3e97fd106d34e12aafd703dada50318
Source dataset
uspto-grants-1996_03
Patent number
US05496949

Reaction notes

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