Pyridine → 2,3-Bis-(acetamido)-6-chloroquinoxaline

HRID 1288222Notes

Reaction equation

HRID 1288222 reaction equation
[C:1](Cl)(=[O:3])[CH3:2].[Cl:5][C:6]1[CH:7]=[C:8]2[C:13](=[CH:14][CH:15]=1)[N:12]=[C:11]([NH2:16])[C:10]([NH2:17])=[N:9]2.N1C=CC=CC=1.[O:24]1CC[CH2:26][CH2:25]1>>[C:1]([NH:16][C:11]1[C:10]([NH:17][C:25](=[O:24])[CH3:26])=[N:9][C:8]2[C:13](=[CH:14][CH:15]=[C:6]([Cl:5])[CH:7]=2)[N:12]=1)(=[O:3])[CH3:2]

Participants

5

Reactant 4

HCID 1049PyridineHCID 6367Acetyl chlorideHCID 8028Tetrahydrofuran2×HCID 125173906-Chloroquinoxaline-2,3-diamine

Product 1

HCID 215045772,3-Bis-(acetamido)-6-chloroquinoxaline

Procedure

To a solution of 33 parts of acetyl chloride in 44 parts of tetrahydrofuran were added 10 parts of 6-chloro-2,3-diaminoquinoxaline. The temperature rose to 35°. The reaction mixture was cooled to 5° in an ice bath and stirred vigorously during the addition of a solution of 15 parts of pyridine in 22 parts of tetrahydrofuran. The cooling bath was removed and the reaction mixture was stirred for 6 hours. The solvent was evaporated and the residue was partitioned between 340 parts of methylene chloride and 200 parts of water. The methylene chloride layer was separated and washed in succession with 200 parts each of water, 10% aqueous sodium carbonate, water, 3% aqueous hydrochloric acid, and water. The methylene chloride solution was dried (MgSO4) and evaporated. The residue was triturated with ether, filtered off, and washed with ether to yield 1.6 parts of 2,3-bis-(acetamido)-6-chloroquinoxaline as a tan solid, m.p. 178° dec.

Workup

  1. customrose to 35°
  2. temperatureThe reaction mixture was cooled to 5° in an ice bath
  3. customThe cooling bath was removed
  4. customThe solvent was evaporated
  5. customthe residue was partitioned between 340 parts of methylene chloride and 200 parts of water
  6. customThe methylene chloride layer was separated
  7. washwashed in succession with 200 parts each of water, 10% aqueous sodium carbonate, water, 3% aqueous hydrochloric acid, and water
  8. dry with materialThe methylene chloride solution was dried (MgSO4)
  9. customevaporated
  10. customThe residue was triturated with ether
  11. filtrationfiltered off
  12. washwashed with ether

Sources & evidence

ORD record
ord-dda78746050f4c80bf77112dcea9cfcb
Source dataset
uspto-grants-1976_10
Patent number
US03987171

Reaction notes

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