Ethyl iodoacetate → HCID 19958587, compound

HRID 373768Notes

Reaction equation

HRID 373768 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[Cl:12])[NH:8][C:7](=[O:13])[CH:6]=[N:5]2.I[CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17]>C(O)C>[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[Cl:12])[N:8]([CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17])[C:7](=[O:13])[CH:6]=[N:5]2

Participants

4

Reactant 2

HCID 12183Ethyl iodoacetateHCID 144236366,7-Dichloroquinoxalin-2(1H)-one

Product 1

HCID 19958587HCID 19958587, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Under a nitrogen atmosphere Na (0.25 g, 11 mmol) was dissolved in 100 ml of abs. ethanol and 6,7-dichloroquinoxalin-2(1H)-one (2.15 g, 10 mmol) (Liebigs Ann. Chem., (1982), 754) was added. The mixture was refluxed for 30 min., cooled to room temperature, and ethyl iodoacetate (1.43 ml, 12 mmol) was added. The clear reaction mixture was refluxed for 2 h during which time a precipitate was formed. This was filtered off, washed with abs. ethanol and dried to afford 2.56 g (85%) of 6,7-dichloro-1-ethoxycarbonylmethylquinoxalin-2(1H)-one. 1H-NMR (DMSO-d6):δ1.23 (t, 3H), 4.20 (q, 2H), 5.08 (s, 2H), 8.05 (s, 1H), 8.17 (s, 1H), 8.38 (s, 1H).

Workup

  1. temperatureThe mixture was refluxed for 30 min.
  2. temperatureThe clear reaction mixture was refluxed for 2 h during which time a precipitate
  3. customwas formed
  4. filtrationThis was filtered off
  5. washwashed with abs
  6. dry with materialethanol and dried

Sources & evidence

ORD record
ord-f8d086ae913e4bd7b81399eccba134ce
Source dataset
uspto-grants-1992_11
Patent number
US05166155

Reaction notes

Loading…