Water → HCID 13337039, compound

HRID 128401Notes

Reaction equation

HRID 128401 reaction equation
[C:1]([C:3]1[C:8]([C:9]#[N:10])=[N:7][C:6]([NH:11][CH2:12][CH3:13])=[C:5](Cl)[N:4]=1)#[N:2].[C:15]1([OH:21])[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.[OH-].[K+].O>O1CCCC1>[C:1]([C:3]1[C:8]([C:9]#[N:10])=[N:7][C:6]([NH:11][CH2:12][CH3:13])=[C:5]([O:21][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[N:4]=1)#[N:2]

Participants

6

Reactant 4

HCID 962WaterHCID 996PhenolHCID 14797Potassium HydroxideHCID 13337056HCID 13337056, compound

Product 1

HCID 13337039HCID 13337039, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

2,3-Dicyano-5-ethylamino-6-chloropyrazine (2.07 g; 0.01 mole) was dissolved in 40 ml of tetrahydrofuran. The solution was cooled to 0° to 5° C., and with stirring, a solution prepared from 0.94 g (0.01 mole) of phenol, 0.56 g (0.01 mole) of potassium hydroxide, 5 ml of water and 20 ml of tetrahydrofuran was added dropwise over the period of 10 minutes. Then, the mixture was stirred at 0° to 5° C. for 1 hour. After the reaction, the precipitate was separated by filtration. The filtrate was concentrated under reduced pressure, and the residue was poured into 80 ml of water. The precipitated crystals were collected by filtration, and recrystallized from benzene to afford 2.22 g (yield 84%) of 2,3-dicyano-5-ethylamino-6-phenoxypyrazine.

Workup

  1. temperatureThe solution was cooled to 0° to 5° C.
  2. additionwas added dropwise over the period of 10 minutes
  3. stirringThen, the mixture was stirred at 0° to 5° C. for 1 hour
  4. customAfter the reaction
  5. customthe precipitate was separated by filtration
  6. concentrationThe filtrate was concentrated under reduced pressure
  7. additionthe residue was poured into 80 ml of water
  8. filtrationThe precipitated crystals were collected by filtration
  9. customrecrystallized from benzene

Sources & evidence

ORD record
ord-bfa93faecbb1413b8d9184abf1bf2152
Source dataset
uspto-grants-1981_03
Patent number
US04259489

Reaction notes

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