Benzoin → 2,3-Diphenylpyrazine

HRID 1868208Notes

Reaction equation

HRID 1868208 reaction equation
[C:1]1([C:7]([CH:9]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)O)=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[NH:17]([CH2:24][CH2:25][NH:26]C1C=CC=CC=1)C1C=CC=CC=1>C1(C)C(C)=CC=CC=1>[C:1]1([C:7]2[C:9]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)=[N:17][CH:24]=[CH:25][N:26]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 8400BenzoinHCID 67422N,N'-Diphenylethylenediamine

Product 1

HCID 2439072,3-DiphenylpyrazineYield 160.8%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Conditions

Temperature
130 °C

Procedure

Bis-phenyl pyrazine was prepared by heating at 130° C. for 12 hrs a suspension of benzoin (Aldrich, 1.25 g) and 1,2 dianilinoethane (Aldrich, 2.13 g) in xylene (20 ml). The mixture was cooled to room temperature and was purified by column chromatography (silicagel, hexane:ethyl acetate, 95:5) to give 2.2 grams of pure bis-phenyl pyrazine as pale yellow solid. NMR: (CDCl3) 7.2-6.8 (20H, m) and 3.6 (4H, s).

Workup

  1. customBis-phenyl pyrazine was prepared
  2. temperatureThe mixture was cooled to room temperature
  3. customwas purified by column chromatography (silicagel, hexane:ethyl acetate, 95:5)

Sources & evidence

ORD record
ord-cfbd49ed0bea404caa2aace8c71d9aa8
Source dataset
uspto-grants-2009_12
Patent number
US07635571B2

Reaction notes

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