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

HRID 1440016Notes

Reaction equation

HRID 1440016 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].C(N(CC)CC)C>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 8471TriethylamineHCID 87885Chloromethyl pivalateHCID 23709643HCID 23709643, compound

Product 1

HCID 10331752Pyrazinecarboxylic acid, (2,2-dimethyl-1-oxopropoxy)methyl esterYield 72.2%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A four-necked flask was charged with 14.6 g (0.10 mole) of sodium pyrazinecarboxylate, 15.1 g (0.10 mole) of chloromethyl pivalate and 1.0 g (0.01 mole) of triethylamine and the charge was maintained under stirring at 98°-100° C. for 6 hours. The reaction mixture was then cooled and 100 ml of toluene was added. The solids (sodium chloride) were filtered off. From the filtrate thus obtained the toluene was distilled off and the filtrate was subjected to distillation under reduced pressure to give 17.2 g of pivaloyloxymethyl pyrazinecarboxylate. Yield: 72%

Workup

  1. temperaturethe charge was maintained
  2. temperatureThe reaction mixture was then cooled
  3. filtrationThe solids (sodium chloride) were filtered off
  4. customFrom the filtrate thus obtained the toluene
  5. distillationwas distilled off
  6. distillationthe filtrate was subjected to distillation under reduced pressure

Sources & evidence

ORD record
ord-4ad07fb905c94c119f988e96b78b1c4c
Source dataset
uspto-grants-1996_03
Patent number
US05496949

Reaction notes

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