3-Phenylphenol → 2-Chloro-6-(3-phenyl-phenyl-oxy)-pyrazine

HRID 16282

Reaction equation

HRID 16282 reaction equation
Cl[C:2]1[CH:7]=[N:6][CH:5]=[C:4]([Cl:8])[N:3]=1.[C:9]1([C:15]2[CH:16]=[C:17]([OH:21])[CH:18]=[CH:19][CH:20]=2)[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1>CCOC(C)=O.C1CCCCC1>[Cl:8][C:4]1[CH:5]=[N:6][CH:7]=[C:2]([O:21][C:17]2[CH:18]=[CH:19][CH:20]=[C:15]([C:9]3[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=3)[CH:16]=2)[N:3]=1

Participants

5

Reactant 2

HCID 113813-PhenylphenolHCID 785042,6-Dichloropyrazine

Product 1

HCID 593435012-Chloro-6-(3-phenyl-phenyl-oxy)-pyrazineYield 98%

Reagents, catalysts & solvents 2

HCID 8078CyclohexaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

Using Method DD (reaction time: 20 hours) with 2,6-dichloropyrazine (200 mg, 1.34 mmol) and 3-phenyl-phenol (268 mg, 1.49 mmol), and purification by column chromatography (AcOEt:cyclohexane, 1:2), the title compound was obtained (370 mg). Yield: 98%. 1H NMR (250 MHz, DMSO-d6) δ 7.35-7.72 (m, 9H, Harom), 8.53 (s, 1H, HPz 5), 8.59 (s, 1H, HPz 3). m/z: 283.1 [(M+H)+, calcd for C16H11ClN2O 282.1].

Workup

  1. customMethod DD (reaction time: 20 hours)

Sources & evidence

ORD record
ord-972732bdf86442079eb9f350a6bbc995
Source dataset
uspto-grants-2010_06
Patent number
US07737152B2

Linked notes

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