Pyridine → 6-Chloro-2,3-bis-(valeramido)quinoxaline

HRID 1288223Notes

Reaction equation

HRID 1288223 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]([NH2:12])[C:6]([NH2:13])=[N:5]2.N1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.[C:20](Cl)(=[O:25])[CH2:21][CH2:22][CH2:23][CH3:24].[O:27]1CCCC1>O>[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]([NH:12][C:15](=[O:27])[CH2:16][CH2:17][CH2:18][CH3:19])[C:6]([NH:13][C:20](=[O:25])[CH2:21][CH2:22][CH2:23][CH3:24])=[N:5]2

Participants

6

Reactant 4

HCID 1049PyridineHCID 8028TetrahydrofuranHCID 61186Valeryl chlorideHCID 125173906-Chloroquinoxaline-2,3-diamine

Product 1

HCID 215045946-Chloro-2,3-bis-(valeramido)quinoxaline

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A suspension of 100 parts of 6-chloro-2,3-diaminoquinoxaline in 1000 parts of pyridine was cooled to 5° in an ice bath. A solution of 152 parts of valeryl chloride in 130 parts of tetrahydrofuran was added quickly with good cooling to prevent the temperature from rising above 20°. The reaction mixture was stirred at ambient temperature for 1 hour and then poured into 2500 parts of water. The solid which separated was removed by filtration and washed with water, methanol, and then ether. The crude product was recrystallized from methanol to yield 55 parts of 6-chloro-2,3-bis-(valeramido)quinoxaline, m.p. 171°-173°, as a colorless solid.

Workup

  1. temperaturewas cooled to 5° in an ice bath
  2. temperaturewith good cooling
  3. customfrom rising above 20°
  4. customThe solid which separated
  5. customwas removed by filtration
  6. washwashed with water, methanol
  7. customThe crude product was recrystallized from methanol

Sources & evidence

ORD record
ord-1c884f5958454788aaa90f22eeeb7d52
Source dataset
uspto-grants-1976_10
Patent number
US03987171

Reaction notes

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