Hydrochloric Acid → HCID 19808448, compound

HRID 373780Notes

Reaction equation

HRID 373780 reaction equation
[Na].[Cl:2][C:3]1[CH:4]=[C:5]2[C:10](=[C:11]([Cl:13])[CH:12]=1)[NH:9][C:8](=[O:14])[CH:7]=[N:6]2.I[CH2:16][C:17]([O:19][CH2:20][CH3:21])=[O:18].Cl>C(O)C>[CH2:20]([O:19][C:17]([CH2:16][N:9]1[C:10]2[C:5](=[CH:4][C:3]([Cl:2])=[CH:12][C:11]=2[Cl:13])[N:6]=[CH:7][C:8]1=[O:14])=[O:18])[CH3:21]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 12183Ethyl iodoacetateHCID 5360545SodiumHCID 15667659HCID 15667659, compound

Product 1

HCID 19808448HCID 19808448, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Under a nitrogen atmosphere sodium (0.13 g, 5.62 mmol) was dissolved in 25 ml of abs. ethanol and 6,8-dichloroquinoxalin-2(1H)-one (1.10 g, 5.11 mmol) was added. The mixture was refluxed for 20 min., and ethyl iodoacetate (0.729 ml, 6.13 mmol) was added. The reaction mixture was refluxed for 72 h, cooled to room temperature, then poured onto crushed ice and acidified by dilute hydrochloric acid (pH=2). The precipitated compound was extracted with dichloromethane (4×30 ml) and purified by column chromatography on silica gel (eluent 10% THF in heptane) to give 1-ethoxycarbonylmethyl-6,8-dichloroquinoxalin-2(1H)-one. 1H-NMR (DMSO-d6):δ1.23 (t, 3H), 4.22 (q, 2H), 5.29 (s, 2H), 7.97 (dd, 2H), 8.45 (s, 1H).

Workup

  1. temperatureThe mixture was refluxed for 20 min.
  2. temperatureThe reaction mixture was refluxed for 72 h
  3. additionpoured
  4. customonto crushed ice
  5. extractionThe precipitated compound was extracted with dichloromethane (4×30 ml)
  6. custompurified by column chromatography on silica gel (eluent 10% THF in heptane)

Sources & evidence

ORD record
ord-1731b7f2d4dc4ba9b1c6b1574be3e286
Source dataset
uspto-grants-1992_11
Patent number
US05166155

Reaction notes

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