Triethylamine → HCID 12907207, compound

HRID 1462285Notes

Reaction equation

HRID 1462285 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]=[C:14]([Cl:18])[CH:13]=2)[N:4]=1)#[N:2].P(Cl)(Cl)([Cl:21])=O.C(N(CC)CC)C>>[C:1]([C:3]1[C:8]([C:9]#[N:10])=[N:7][C:6]([Cl:21])=[C:5]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([Cl:18])[CH:13]=2)[N:4]=1)#[N:2]

Participants

4

Reactant 3

HCID 8471TriethylamineHCID 24813Phosphorus oxychlorideHCID 178510650HCID 178510650, compound

Product 1

HCID 12907207HCID 12907207, compoundYield 84%

Procedure

2,3-Dicyano-5-hydroxy-6-(m-chlorophenyl)pyrazine (25.67 g; 0.10 mole) was put into 46.2 g (0.30 mole) of phosphorus oxychloride. The mixture was cooled to 0° to 5° C., and with stirring 10.1 g (0.1 mole) of triethylamine was added dropwise over the period of 30 minutes. After the addition, the mixture was refluxed for 3 hours. The reaction mixture was worked up in the same way as in Example 3. Petroleum ether (50 ml) was added to the resulting oily product, and the precipitate was collected by filtration. Recrystallization from carbon tetrachloride afforded 23.1 g (yield 83%) of 2,3-dicyano-5-chloro-6-(m-chlorophenyl)pyrazine.

Workup

  1. temperatureThe mixture was cooled to 0° to 5° C.
  2. additionwas added dropwise over the period of 30 minutes
  3. additionAfter the addition
  4. temperaturethe mixture was refluxed for 3 hours
  5. filtrationthe precipitate was collected by filtration
  6. customRecrystallization from carbon tetrachloride

Sources & evidence

ORD record
ord-6a29c36dab0f48739947fe264e926622
Source dataset
uspto-grants-1984_07
Patent number
US04460403

Reaction notes

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