Ammonia → 5-Amino-6-chloro-2,3-dicyanopyrazine

HRID 2371379Notes

Reaction equation

HRID 2371379 reaction equation
[Cl:1][C:2]1[C:7](Cl)=[N:6][C:5]([C:9]#[N:10])=[C:4]([C:11]#[N:12])[N:3]=1.[NH3:13].O>O1CCCC1>[NH2:13][C:7]1[C:2]([Cl:1])=[N:3][C:4]([C:11]#[N:12])=[C:5]([C:9]#[N:10])[N:6]=1

Participants

5

Reactant 3

HCID 222AmmoniaHCID 962WaterHCID 6078205,6-Dichloro-2,3-dicyanopyrazine

Product 1

HCID 6016455-Amino-6-chloro-2,3-dicyanopyrazineYield 93.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

5.0 g (0.025 mol) of 2,3-dichloro-5,6-dicyanopyrazine was dissolved in 50 ml of dry tetrahydrofuran, and 6.1 g (0.050 mol) of 28% aqueous ammonia was dropwise added at a temperature of from -15°to 0° C. After completion of the dropwise addition, the mixture was stirred for 1 hour, and the reaction solution was poured into 500 ml of water. The precipitated solid was collected by filtration and recrystallized from a solvent mixture of toluene and ethyl acetate to obtain 4.2 g of slightly yellow crystals (yield: 93.6%, melting point: 205-208° C.).

Workup

  1. additionAfter completion of the dropwise addition
  2. filtrationThe precipitated solid was collected by filtration
  3. customrecrystallized from a solvent mixture of toluene and ethyl acetate

Sources & evidence

ORD record
ord-61d8ceb931cc41acaaa0f1ef8ac13fac
Source dataset
uspto-grants-1992_03
Patent number
US05093335

Reaction notes

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