Phenoxyethanol → HCID 18186845, compound

HRID 1357587Notes

Reaction equation

HRID 1357587 reaction equation
Cl[C:2]1[CH:7]=[N:6][CH:5]=[C:4]([Cl:8])[N:3]=1.[O:9]([CH2:16][CH2:17][OH:18])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1>O1CCOCC1>[Cl:8][C:4]1[CH:5]=[N:6][CH:7]=[C:2]([O:18][CH2:17][CH2:16][O:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[N:3]=1

Participants

4

Reactant 2

HCID 31236PhenoxyethanolHCID 785042,6-Dichloropyrazine

Product 1

HCID 18186845HCID 18186845, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

K-t-BuO (1.61 g, 14.3 mmol) was added portionwise to a stirred mixture of 2,6-dichloropyrazine (2.03 g, 13.6 mmol) and 2-phenoxyethanol (2.54 g, 18.4 mmol) in dioxane (8 mL) at 0° C. (ice-bath). After 5 min of stirring, the ice-bath was removed and the mixture was stirred at room temperature for 1 h. The reaction mixture was diluted with ether, filtered and concentrated in vacuo. The oily residue was purified by silica gel chromatography (18×5 cm) using n-hexane/ethyl acetate (92:8) as eluent. This furnished 2.92 g (86%) of the title compound as a white solid. HRMS m/z calcd for C12H11ClN2O2 (M)+ 250.0509, found 250.0511. Anal. (C12H11ClN2O2) C, H, N.

Workup

  1. customthe ice-bath was removed
  2. stirringthe mixture was stirred at room temperature for 1 h
  3. additionThe reaction mixture was diluted with ether
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe oily residue was purified by silica gel chromatography (18×5 cm)

Sources & evidence

ORD record
ord-e3f360486fcd47218b74db70a7085f6d
Source dataset
uspto-grants-2003_07
Patent number
US06593330B2

Reaction notes

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