Dimethylformamide → HCID 86667412, compound

HRID 1429091Notes

Reaction equation

HRID 1429091 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[CH:3]=[C:2]1[C:10]1[C:11](O)=[N:12][C:13]2[C:18]([N:19]=1)=[CH:17][CH:16]=[CH:15][CH:14]=2.S(Cl)([Cl:23])=O.CN(C=O)C>C1(C)C=CC=CC=1.ClCCl>[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[CH:3]=[C:2]1[C:10]1[C:11]([Cl:23])=[N:12][C:13]2[C:18](=[CH:17][CH:16]=[CH:15][CH:14]=2)[N:19]=1

Participants

6

Reactant 3

HCID 6228DimethylformamideHCID 24386Thionyl ChlorideHCID 178517134HCID 178517134, compound

Product 1

HCID 86667412HCID 86667412, compoundYield 103.7%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
110 °C

Procedure

To a suspension of 3-(benzofuran-2-yl)quinoxalin-2-ol (Example 15b, 268 mg, 1.02 mmol) in Toluene (5.1 mL) was added thionyl chloride (0.30 mL, 4.1 mmol) followed by DMF (238 μl, 3.07 mmol). The yellow reaction mixture was stirred at 110° C. for 2 h, cooled to room temperature, and evaporated under reduced pressure to gave a yellow solid. The solid was suspended in dichloromethane (20 ml) and purified by flash chromatography on silica gel (dichloromethane) to give the title compound, 2-(benzofuran-2-yl)-3-chloroquinoxaline (297 mg, quantitative yield), as a yellow solid.

Workup

  1. temperaturecooled to room temperature
  2. customevaporated under reduced pressure
  3. customto gave a yellow solid
  4. custompurified by flash chromatography on silica gel (dichloromethane)

Sources & evidence

ORD record
ord-3840cddfd94d420e80c9951fa949c0d4
Source dataset
uspto-grants-2015_01
Patent number
US08937041B2

Reaction notes

Loading…