2-Chloroethanol → HCID 14881239, compound

HRID 1904333Notes

Reaction equation

HRID 1904333 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-dimethylpyrazine (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 wit 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 wit 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-c2536c0d62e94c9e968f7e051ab026e6
Source dataset
uspto-grants-1989_06
Patent number
US04837319

Reaction notes

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