3-Hydroxyacetanilide → 2-Chloro-6-(3-acetamidophenyl-oxy)-pyrazine

HRID 16284

Reaction equation

HRID 16284 reaction equation
Cl[C:2]1[CH:7]=[N:6][CH:5]=[C:4]([Cl:8])[N:3]=1.[C:9]([NH:12][C:13]1[CH:14]=[C:15]([OH:19])[CH:16]=[CH:17][CH:18]=1)(=[O:11])[CH3:10]>CCOC(C)=O>[Cl:8][C:4]1[CH:5]=[N:6][CH:7]=[C:2]([O:19][C:15]2[CH:16]=[CH:17][CH:18]=[C:13]([NH:12][C:9](=[O:11])[CH3:10])[CH:14]=2)[N:3]=1

Participants

4

Reactant 2

HCID 121243-HydroxyacetanilideHCID 785042,6-Dichloropyrazine

Product 1

HCID 115435012-Chloro-6-(3-acetamidophenyl-oxy)-pyrazineYield 99%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Using Method DD with 2,6-dichloropyrazine (200 mg, 1.34 mmol) and 3-acetamidophenol (202 mg, 1.49 mmol), and crystallisation in AcOEt, the title compound was obtained (350 mg). Yield: 99%. 1H NMR (250 MHz, DMSO-d6) δ 2.06 (s, 3H, CH3—NH), 6.90-6.95 (m, 1H, Harom 5), 7.76 (dd, 2H, Harom 4+6, Jm=2.0 Hz, Jo=7.6 Hz), 7.59 (s, 1H, Harom 2), 8.52 (s, 1H, HPz 5), 8.54 (s, 1H, HPz 3), 10.12 (s, 1H, NH).

Sources & evidence

ORD record
ord-e6a0f051b628495cba8a3695804c12d5
Source dataset
uspto-grants-2010_06
Patent number
US07737152B2

Linked notes

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