Acetyl chloride → 1-Ethyl-2-methyl-5,6-diphenyl-1H-imidazo[4,5-b]pyrazine

HRID 436204Notes

Reaction equation

HRID 436204 reaction equation
Cl[C:2]1[C:7]([NH:8][CH2:9][CH3:10])=[N:6][C:5]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[C:4]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[N:3]=1.[CH2:23]([N:25](CC)CC)[CH3:24].C(Cl)(=O)C>C1C=CC=CC=1.C(O)C>[CH2:9]([N:8]1[C:7]2=[N:6][C:5]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)=[C:4]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[N:3]=[C:2]2[N:25]=[C:23]1[CH3:24])[CH3:10]

Participants

6

Reactant 3

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 214548043-Chloro-N-ethyl-5,6-diphenyl-2-pyrazinamine

Product 1

HCID 214547901-Ethyl-2-methyl-5,6-diphenyl-1H-imidazo[4,5-b]pyrazine

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 702EthanolSolvent

Conditions

Temperature
15 °C

Procedure

2-Chloro-3-ethylamino-5,6-diphenylpyrazine, (3.10 g, 0.01 moles) is dissolved in benzene (50 ml) and then triethylamine (1.29 g, 0.013 moles) and acetyl chloride (1.00 g, 0.013 moles) are added. The solution is refluxed 41/2 hours, cooled to 15° C and filtrate. The filtrate is diluted with ethanol (3 ml), warmed briefly at 50° C and then all volatile materials evaporated. The resultant brown oil is treated with liquid ammonia (17 g) in ethanol (60 ml) in a bomb at 165° C for 12 hours. The solution is diluted with water (200 ml), cooled and the yellow precipitate filtered off. The solid is triturated with boiling 50% aqueous methanol, filtered, and the filtrate chilled. The product is collected by filtration. Yield 0.45 g (14%). It is recrystallized from benzene-heptane, m.p. 178.5°-180° C.

Workup

  1. temperatureThe solution is refluxed 41/2 hours
  2. temperaturewarmed briefly at 50° C
  3. customall volatile materials evaporated
  4. additionThe resultant brown oil is treated with liquid ammonia (17 g) in ethanol (60 ml) in a bomb at 165° C for 12 hours
  5. additionThe solution is diluted with water (200 ml)
  6. temperaturecooled
  7. filtrationthe yellow precipitate filtered off
  8. customThe solid is triturated
  9. filtrationfiltered
  10. temperaturethe filtrate chilled
  11. filtrationThe product is collected by filtration
  12. customIt is recrystallized from benzene-heptane, m.p. 178.5°-180° C.

Sources & evidence

ORD record
ord-b5b1e2cf8de0479fa06be2ab4f999950
Source dataset
uspto-grants-1977_02
Patent number
US04007170

Reaction notes

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