Formaldehyde → 1-Methyl-3-(2-hydroxyethyl)pyrazinium iodide

HRID 980467Notes

Reaction equation

HRID 980467 reaction equation
[OH:1][CH2:2][CH2:3][C:4]1[CH:9]=[N:8][CH:7]=[CH:6][N:5]=1.C=O.[CH3:12]C1C=NC=CN=1.C[I:20]>CO>[I-:20].[CH3:12][N+:8]1[CH:7]=[CH:6][N:5]=[C:4]([CH2:3][CH2:2][OH:1])[CH:9]=1

Participants

6

Reactant 4

HCID 712FormaldehydeHCID 6328Methyl iodideHCID 79762-MethylpyrazineHCID 5222472-(pyrazin-2-yl)ethanol

Product 1

HCID 202215661-Methyl-3-(2-hydroxyethyl)pyrazinium iodide

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

2.0 g of 2-(2-hydroxyethyl)pyrazine (301) prepared by a known method by condensing formaldehyde and 2-methylpyrazine, was dissolved in 5 ml of methanol and 5 ml of methyl iodide added. The solution was refluxed for 3 days, concentrated and the residue purified by gel permeation chromatography. Freeze-drying gave 3.2 g of yellow solid product (300). It was recrystallized from ethyl acetate/ethanol, m.p. 94°-5°. UV H2O max: 226 (4.13), 281 (3.85). 13C NMR: 163.25, S (C3); 150.71, D (C5); 138.69, D, 136.25, D (C2, C6); 60.38, T (CH2OH); 49.88, Q (NCH3); 38.75, T (--CH2 --). 1H NMR: 9.35, D, T (H6); 8.97, S (H2); 8.85, D (H5); 4.49, S (NCH3); 4.08, T; 3.35, T (ArCH2, CH2OH).

Workup

  1. temperatureThe solution was refluxed for 3 days
  2. concentrationconcentrated
  3. customthe residue purified by gel permeation chromatography
  4. customFreeze-drying

Sources & evidence

ORD record
ord-01e164144c3c4545ae01c0a29164a685
Source dataset
uspto-grants-1987_01
Patent number
US04638005

Reaction notes

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