Triethylamine → 5-Chloro-6-phenylpyrazine-2,3-dicarbonitrile

HRID 1462284

Reaction equation

HRID 1462284 reaction equation
[C:1]([C:3]1[C:8]([C:9]#[N:10])=[N:7][C:6](O)=[C:5]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[N:4]=1)#[N:2].P(Cl)(Cl)([Cl:20])=O.C(N(CC)CC)C>>[C:1]([C:3]1[C:8]([C:9]#[N:10])=[N:7][C:6]([Cl:20])=[C:5]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[N:4]=1)#[N:2]

Participants

4

Reactant 3

HCID 8471TriethylamineHCID 24813Phosphorus oxychlorideHCID 1785106496-Oxo-5-phenyl-1,6-dihydropyrazine-2,3-dicarbonitrile

Product 1

HCID 129072055-Chloro-6-phenylpyrazine-2,3-dicarbonitrileYield 80.5%

Procedure

The 2,3-dicyano-5-hydroxy-6-phenylpyrazine (7.00 g; 0.0315 mole) was dissolved in 40.00 g (0.26 mole) of phosphorus oxychloride, and while the solution was cooled to 5° to 10° C., 3.53 g (0.035 mole) of triethylamine was added dropwise over the period of 20 minutes. After the addition, the mixture was stirred at 70° to 80° C. for 1.5 hours. The reaction mixture was worked up in the same way as in Example 3, and recrystallized from benzene to afford 6.10 g (yield 80%) of 2,3-dicyano-5-chloro-6-phenylpyrazine.

Workup

  1. temperaturewhile the solution was cooled to 5° to 10° C.
  2. additionAfter the addition
  3. customrecrystallized from benzene

Sources & evidence

ORD record
ord-fa997e7e70594797bdc57a801bf77a6b
Source dataset
uspto-grants-1984_07
Patent number
US04460403

Linked notes

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