Dichloromethane → HCID 18186880, compound

HRID 1357611Notes

Reaction equation

HRID 1357611 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[CH:9]([OH:11])[CH3:10].[Cl:12][C:13]1[CH:18]=[N:17][CH:16]=[C:15](Cl)[N:14]=1.ClCCl.C([O-])([O-])=O.[K+].[K+]>O1CCOCC1>[Cl:12][C:13]1[CH:18]=[N:17][CH:16]=[C:15]([O:11][CH:9]([C:4]2[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=2[O:2][CH3:1])[CH3:10])[N:14]=1

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 11430Potassium CarbonateHCID 785042,6-DichloropyrazineHCID 1145381-(2-Methoxyphenyl)ethan-1-ol

Product 1

HCID 18186880HCID 18186880, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

K-t-BuO (0.67 g, 5.97 mmol) was added to a stirred solution of 1-(2-methoxyphenyl)ethanol (0.96 g, 6.28 mmol) in dioxane (15 mL) at 0° C. (ice-bath). After 5 min of stirring at room temperature, the reaction mixture was chilled to 0° C. (ice-bath) and 2,6-dichloropyrazine (0.78 g, 5.23 mmol) was added whereupon the reaction mixture turned yellow. After being stirred for 35 min, dichloromethane and K2CO3 were added and the mixture was filtered. Concentration in vacuo furnished a yellow oil that was purified by silica gel chromatography (15×4 cm) using n-hexane ethyl acetate (8:2) as eluent. This gave 1.21 g (92%) of the title compound as a colorless oil. HRMS m/z calcd for C13H13ClN2O2 (M)+ 264.0666, found 264.0677. Anal. (C13H13ClN2O2) C, H, N.

Workup

  1. additionwas added whereupon the reaction mixture
  2. stirringAfter being stirred for 35 min
  3. filtrationthe mixture was filtered
  4. concentrationConcentration in vacuo
  5. customfurnished a yellow oil that
  6. customwas purified by silica gel chromatography (15×4 cm)

Sources & evidence

ORD record
ord-78aae964805a4a6b9cb2db6be1316e53
Source dataset
uspto-grants-2003_07
Patent number
US06593330B2

Reaction notes

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