Sodium Methoxide → HCID 20483476, compound

HRID 647965Notes

Reaction equation

HRID 647965 reaction equation
[Cl:1][C:2]1[C:3]([O:8][CH2:9][CH:10]([OH:16])[CH2:11][NH:12][CH:13]([CH3:15])[CH3:14])=[N:4][CH:5]=[CH:6][N:7]=1.[CH3:17][O-:18].[Na+]>CO>[ClH:1].[CH3:17][O:18][C:2]1[C:3]([O:8][CH2:9][CH:10]([OH:16])[CH2:11][NH:12][CH:13]([CH3:15])[CH3:14])=[N:4][CH:5]=[CH:6][N:7]=1

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 204834181-[(3-Chloropyrazin-2-yl)oxy]-3-[(propan-2-yl)amino]propan-2-ol

Product 1

HCID 20483476HCID 20483476, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

7.5 g of 3-chloro-2-(3'-isopropylamino-2'-hydroxy-propoxy)-pyrazine and 3.2 g of sodium methylate in 150 ml of methanol are boiled for 10 hours under reflux. The reaction mixture is then evaporated in a waterpump vacuum. The residue is partitioned between 2 N hydrochloric acid and ether. The acid aqueous phase is rendered alkaline with concentrated sodium hydroxide solution and extracted by shaking with ether. The ether extracts are washed with water, dried over sodium sulphate and evaporated in a waterpump vacuum. The crude base is thus obtained, from which 3-methoxy-2-(3'-isopropylamino-2'-hydroxy-propoxy)-pyrazine hydrochloride, melting point 152°-153° C., is obtained by reaction with ethereal hydrochloric acid in methanol.

Workup

  1. temperatureunder reflux
  2. customThe reaction mixture is then evaporated in a waterpump vacuum
  3. customThe residue is partitioned between 2 N hydrochloric acid and ether
  4. extractionextracted
  5. washThe ether extracts are washed with water
  6. dry with materialdried over sodium sulphate
  7. customevaporated in a waterpump vacuum

Sources & evidence

ORD record
ord-470077ae79644c2f9eeb6193bd849d25
Source dataset
uspto-grants-1983_10
Patent number
US04410530

Reaction notes

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