Ethylamine → 3-Chloro-N-ethyl-5,6-diphenyl-2-pyrazinamine

HRID 436203Notes

Reaction equation

HRID 436203 reaction equation
Cl[C:2]1[C:7]([Cl:8])=[N:6][C:5]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[C:4]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[N:3]=1.[CH2:21]([NH2:23])[CH3:22]>CN(C)C=O.O>[Cl:8][C:7]1[C:2]([NH:23][CH2:21][CH3:22])=[N:3][C:4]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[C:5]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[N:6]=1

Participants

5

Reactant 2

HCID 6341EthylamineHCID 2792282,3-dichloro-5,6-diphenylpyrazine

Product 1

HCID 214548043-Chloro-N-ethyl-5,6-diphenyl-2-pyrazinamine

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent2×

Procedure

2,3-Dichloro-5,6-diphenylpyrazine (2.00 g, 0.0066 moles), is suspended in dimethylformamide (DMF) (12 ml) and treated with a solution of ethylamine (70% in water) (3.5 ml) in DMF (6 ml) and the mixture is warmed at 40°-45° C for 30 minutes then allowed to stand at room temperature for 6 hours. The solution is diluted with water (80 ml) and after standing overnight the solid is filtered off, washed with water and dissolved in hot ethyl alcohol, filtered, concentrated and cooled to yield 1.19 g of greenish-yellow solid. m.p. 115°-122°. This material is recrystallized from an ethyl alcohol-hexane mixture, yield 0.84 g, m.p. 121°-125°. Identity of the product is confirmed by infrared, nuclear magnetic resonance and mass spectra.

Workup

  1. temperaturethe mixture is warmed at 40°-45° C for 30 minutes
  2. waitafter standing overnight
  3. filtrationthe solid is filtered off
  4. washwashed with water
  5. dissolutiondissolved in hot ethyl alcohol
  6. filtrationfiltered
  7. concentrationconcentrated
  8. temperaturecooled

Sources & evidence

ORD record
ord-8fd5e7acaddd4e6ebefec70337c9997d
Source dataset
uspto-grants-1977_02
Patent number
US04007170

Reaction notes

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