Formaldehyde → HCID 4099578, compound

HRID 2052288Notes

Reaction equation

HRID 2052288 reaction equation
[CH3:1][C:2]1[CH:7]=[N:6][CH:5]=[CH:4][N:3]=1.Cl.[CH3:9][NH:10][CH3:11].[CH2:12]=O.[OH-].[Na+]>O>[CH3:9][N:10]([CH3:12])[CH2:11][CH2:1][C:2]1[CH:7]=[N:6][CH:5]=[CH:4][N:3]=1

Participants

6

Reactant 4

HCID 712FormaldehydeHCID 79762-MethylpyrazineHCID 10473Dimethylamine, hydrochlorideHCID 14798Sodium Hydroxide

Product 1

HCID 4099578HCID 4099578, compoundYield 66.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 94.0 g (1.0 mole) of methylpyrazine and 83.9 g (1.03 mole) of dimethylamine hydrochloride was heated until it began refluxing. 131.3 g (40% aqueous solution) (1.75 mole) of formaldehyde was added over a period of two hours. The resulting brown viscous mass was refluxed for additional 2.5 hours. The mixture was cooled to room temperature. It was diluted with 250 ml of water, made basic with 10% sodium hydroxide solution and extracted with chloroform. After removing the chloroform the residue was distilled to give 100.6 g of β-dimethylaminoethylpyrazine, b.p. 116°-120° C. at 20 mm Hg.

Workup

  1. temperaturewas heated until it
  2. temperaturebegan refluxing
  3. temperatureThe resulting brown viscous mass was refluxed for additional 2.5 hours
  4. extractionextracted with chloroform
  5. customAfter removing the chloroform the residue
  6. distillationwas distilled

Sources & evidence

ORD record
ord-b87c55ce4efe481f9fb448202f03e6ed
Source dataset
uspto-grants-1980_01
Patent number
US04183933

Reaction notes

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