2-Chloroethanol → HCID 14881117, compound

HRID 1608328Notes

Reaction equation

HRID 1608328 reaction equation
[CH2:1](Cl)[CH2:2][OH:3].[OH:5][C:6]1[C:11]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[N:10][C:9]([CH3:18])=[C:8]([CH3:19])[N:7]=1.[OH-].[Na+].O>C(O)(C)(C)C>[OH:3][CH2:2][CH2:1][N:7]1[C:8]([CH3:19])=[C:9]([CH3:18])[N:10]=[C:11]([C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)[C:6]1=[O:5]

Participants

6

Reactant 4

HCID 342-ChloroethanolHCID 962WaterHCID 14798Sodium HydroxideHCID 178433435HCID 178433435, compound

Product 1

HCID 14881117HCID 14881117, compoundYield 71.6%

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent

Conditions

Temperature
60 °C

Procedure

Ethylene chlorohydrin (20.2 g, 0.25M) was added to a solution of 2-hydroxy-3-phenyl-5,6-dimethyl-pyrazine (10.0 g, 50 mM) and 5N NaOH (50 ml) in t-butanol (150 ml), and stirred at 60° C. for 2.5 hours. Water was added to the reaction mixture, the mixture extracted with chloroform, and the extract dried with anhydrous sodium sulfate and concentrated in vacuo. The residue was charged on a column of silica-gel (C-200, 130 g) packed with chloroform and eluted with chloroform-methanol (100:1) to obtain compound 109 (8.73 g, yield: 71.5%).

Workup

  1. extractionthe mixture extracted with chloroform
  2. dry with materialthe extract dried with anhydrous sodium sulfate
  3. concentrationconcentrated in vacuo
  4. additionThe residue was charged on a column of silica-gel (C-200, 130 g)
  5. washeluted with chloroform-methanol (100:1)

Sources & evidence

ORD record
ord-6eb0c7a193c84680b7fde7de10e0cc78
Source dataset
uspto-grants-1989_09
Patent number
US04870176

Reaction notes

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