Water → 5-(tert-Butylamino)-6-chloropyrazine-2,3-dicarbonitrile

HRID 2371381Notes

Reaction equation

HRID 2371381 reaction equation
Cl[C:2]1[C:7]([Cl:8])=[N:6][C:5]([C:9]#[N:10])=[C:4]([C:11]#[N:12])[N:3]=1.[C:13]([NH2:17])([CH3:16])([CH3:15])[CH3:14].O>O1CCCC1>[Cl:8][C:7]1[C:2]([NH:17][C:13]([CH3:16])([CH3:15])[CH3:14])=[N:3][C:4]([C:11]#[N:12])=[C:5]([C:9]#[N:10])[N:6]=1

Participants

5

Reactant 3

HCID 962WaterHCID 6385Tert-ButylamineHCID 6078205,6-Dichloro-2,3-dicyanopyrazine

Product 1

HCID 145764275-(tert-Butylamino)-6-chloropyrazine-2,3-dicarbonitrileYield 76.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

5.0 g (0.025 mol) of 2,3-dichloro-5,6-dicyanopyrazine was dissolved in 50 ml of dry tetrahydrofuran, and 25 ml of a dry tetrahydrofuran solution containing 3.7 g (0.050 mol) of tert-butylamine was dropwise added thereto at a temperature of from -15°to 0° C. After completion of the dropwise addition, the mixture was stirred for 2 hours, and the reaction solution was poured into 500 ml of water. The precipitated solid was collected by filtration and recrystallized from toluene to obtain 4.5 g of slightly yellow crystals (yield: 76.4%, melting point: 174°-176° C.).

Workup

  1. additionwas dropwise added
  2. customof from -15°to 0° C
  3. additionAfter completion of the dropwise addition
  4. filtrationThe precipitated solid was collected by filtration
  5. customrecrystallized from toluene

Sources & evidence

ORD record
ord-8ffa0fbbbdd94619a7fe13eb455753fa
Source dataset
uspto-grants-1992_03
Patent number
US05093335

Reaction notes

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