2-Chloroethanol → HCID 14881239, compound

HRID 1608334Notes

Reaction equation

HRID 1608334 reaction equation
[CH2:1](Cl)[CH2:2][OH:3].[OH:5][C:6]1[C:11]([CH2:12][C:13]2[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][CH:14]=2)=[N:10][C:9]([CH3:20])=[C:8]([CH3:21])[N:7]=1>[OH-].[Na+].C(O)(C)(C)C>[OH:3][CH2:2][CH2:1][N:7]1[C:8]([CH3:21])=[C:9]([CH3:20])[N:10]=[C:11]([CH2:12][C:13]2[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][CH:14]=2)[C:6]1=[O:5]

Participants

5

Reactant 2

HCID 342-ChloroethanolHCID 178433446HCID 178433446, compound

Product 1

HCID 14881239HCID 14881239, compoundYield 75.9%

Reagents, catalysts & solvents 2

HCID 6386tert-ButanolSolventHCID 14798Sodium HydroxideSolvent

Conditions

Temperature
60 °C

Procedure

Ethylene chlorohydrin (16.11 g, 0.20M) was added to a solution of 2-hydroxy-3-p-chlorobenzyl-5,6-dimethyl-pyrazine (11.06 g, 40 mM) in aqueous 5N NaOH (40 ml) and t-butanol (120 ml), and stirred at 60° C. for 3 hours. The t-butanol was distilled off in vacuo. Dilute aqueous K2CO3 was added to the residue, the resulting mixture being extracted three times with chloroform, dried with anhydrous sodium sulfate and concentrated in vacuo. The residue was charged on a column of silica-gel (C-200, 300 g) packed with chloroform and eluted with chloroform-methanol (100:1) to obtain compound 641 (9.73 g, yield: 75.9%).

Workup

  1. distillationThe t-butanol was distilled off in vacuo
  2. additionDilute aqueous K2CO3 was added to the residue
  3. extractionthe resulting mixture being extracted three times with chloroform
  4. dry with materialdried with anhydrous sodium sulfate
  5. concentrationconcentrated in vacuo
  6. additionThe residue was charged on a column of silica-gel (C-200, 300 g)
  7. washeluted with chloroform-methanol (100:1)

Sources & evidence

ORD record
ord-c58e3e88f42f445aa3b3d64a4ff47b59
Source dataset
uspto-grants-1989_09
Patent number
US04870176

Reaction notes

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