Reaction #44563

ord-1021f49b714044e99d2cad1994e02d0f

Reaction equation

Clc1cncc(Cl)n1
2,6-dichloropyrazine
CC(=O)Nc1ccc(O)cc1
4-acetamidophenol
→
CC(=O)Nc1ccc(Oc2cncc(Cl)n2)cc1
title compound
Yield 92.0%
CC(=O)Nc1ccc(Oc2cncc(Cl)n2)cc1
2-Chloro-6-(4-acetamidophenyl-oxy)-pyrazine
Yield 92.0%

Reactants

Clc1cncc(Cl)n1
2,6-dichloropyrazine
CC(=O)Nc1ccc(O)cc1
4-acetamidophenol

Reagents

None

Solvents

CCOC(C)=O
AcOEt

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Procedure

Using Method DD with 2,6-dichloropyrazine (200 mg, 1.34 mmol) and 4-acetamidophenol (202 mg, 1.49 mmol), and crystallisation in AcOEt, the title compound was obtained (327 mg). Yield: 92%. 1H NMR (250 MHz, DMSO-d6) δ 2.12 (s, 3H, CH3—NH), 7.25 (d, 2H, Harom 3+5, J=8.9 Hz), 7.71 (d, 2H, Harom 2+6, J=8.9 Hz), 8.55 (s, 1H, HPz 5), 8.57 (s, 1H, HPz 3), 10.10 (s, 1H, NH). m/z: 264.0 [(M+H)+, calcd for C12H10ClN3O2 263.0].

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US07737152B2uspto-grants-2010_06