Ethylenediamine → HCID 178470161, compound

HRID 336354Notes

Reaction equation

HRID 336354 reaction equation
[OH:1][C:2]1[C:3]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[N:4][C:5]2[C:10]([N:11]=1)=[CH:9][C:8](I)=[CH:7][CH:6]=2.[CH3:18][S:19]([O-:21])=[O:20].[Na+].C(N)CN>CS(C)=O.C(OCC)(=O)C>[OH:1][C:2]1[C:3]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[N:4][C:5]2[C:10]([N:11]=1)=[CH:9][C:8]([S:19]([CH3:18])(=[O:21])=[O:20])=[CH:7][CH:6]=2

Participants

6

Reactant 3

HCID 3301EthylenediamineHCID 2733271Sodium methanesulfinateHCID 178470160HCID 178470160, compound

Product 1

HCID 178470161HCID 178470161, compound

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
110 °C

Procedure

A degassed mixture of ethyl 3-hydroxy-6-iodoquinoxaline-2-carboxylate (351 mg, 1.0 mmol), sodium methanesulfinate (132 mg, 1.3 mmol), copper(I) triflate benzene complex (25 mg, 5 mol %) and ethylenediamine (0.01 mL, 10 mol %) in anhydrous DMSO (1.0 mL) was heated at 110° C. in a sealed reaction vessel for 20 h. The cooled mixture was diluted with ethyl acetate (10 mL) and filtered through a plug of silica gel under reduced pressure, eluting with additional ethyl acetate (50 mL). The filtrate was washed with water (20 mL) and brine (20 mL), dried over sodium sulfate and filtered. The solvents were removed under reduced pressure and the residue was purified by flash column chromatography on silica gel, eluting with ethyl acetate, to provide ethyl 3-hydroxy-6-(methylsulfonyl)quinoxaline-2-carboxylate as a yellow solid: 1H NMR (400 MHz, CDCl3) δ 11.61 (br S, 1H), 8.16 (d, J=8.9 Hz, 1H), 8.01 (s, 1H), 7.91 (d, J=9.9 Hz, 1H), 4.58 (q, J=6.7 Hz, 2H), 3.16 (s, 3H), 1.49 (t, J=6.7 Hz) ppm; ESI MS m/z 297 [M+H]−.

Workup

  1. filtrationfiltered through a plug of silica gel under reduced pressure
  2. washeluting with additional ethyl acetate (50 mL)
  3. washThe filtrate was washed with water (20 mL) and brine (20 mL)
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. customThe solvents were removed under reduced pressure
  7. customthe residue was purified by flash column chromatography on silica gel
  8. washeluting with ethyl acetate

Sources & evidence

ORD record
ord-3c0269e70b954c9e8ae4a4ac320f58d8
Source dataset
uspto-grants-2014_11
Patent number
US08889683B2

Reaction notes

Loading…