2,6-Dichloropyrazine → HCID 18186866, compound

HRID 1357597Notes

Reaction equation

HRID 1357597 reaction equation
[CH3:1][N:2]([CH3:12])[C:3]1[CH:11]=[CH:10][C:6]([CH2:7][CH2:8][OH:9])=[CH:5][CH:4]=1.[Cl:13][C:14]1[CH:19]=[N:18][CH:17]=[C:16](Cl)[N:15]=1>O1CCOCC1.ClCCl.CCOCC>[Cl:13][C:14]1[CH:19]=[N:18][CH:17]=[C:16]([O:9][CH2:8][CH2:7][C:6]2[CH:10]=[CH:11][C:3]([N:2]([CH3:1])[CH3:12])=[CH:4][CH:5]=2)[N:15]=1

Participants

5

Reactant 2

HCID 785042,6-DichloropyrazineHCID 93252p-N,N-Dimethylaminophenethanol

Product 1

HCID 18186866HCID 18186866, compoundYield 80%

Reagents, catalysts & solvents 2

HCID 312751,4-DioxaneSolventHCID 21881112Ethyl ether methylene chlorideSolvent

Conditions

Temperature
0 °C

Procedure

K-t-BuO (2.27 g, 20.3 mmol) was added to a stirred solution of 4-(dimethylamino)phenethyl alcohol (3.55 g, 21.5 mmol) in dioxane (35 mL) at 0° C. (ice-bath). After being stirred for 5 min at 0° C. and 12 min at room temperature, the mixture was chilled to 0° C. (ice-bath) and 2,6-dichloropyrazine (2.62 g, 17.6 mmol) was added. The reaction mixture was stirred at 0° C. for 5 min and at room temperature for 20 min and diluted with dichloromethane/ether (1:1). Filtration through a pad of Celite, covered with K2CO3, and concentration in vacuo furnished a yellow oil. This material was purified by chromatography on silica gel (15×5 cm) using n-hexane/ethyl acetate (85:15). A second chromatograhic run on silica gel (14×5 cm) using n-hexane/ethyl acetate (88:12) furnished 3.91 g (80%) of the title compound as a colorless oil. Anal. (C14H16ClN3O) C, H, N.

Workup

  1. additionwas added
  2. stirringThe reaction mixture was stirred at 0° C. for 5 min and at room temperature for 20 min
  3. filtrationFiltration through a pad of Celite
  4. concentrationcovered with K2CO3, and concentration in vacuo
  5. customfurnished a yellow oil
  6. customThis material was purified by chromatography on silica gel (15×5 cm)

Sources & evidence

ORD record
ord-3f365d0c2fa644fd854a269435d8230b
Source dataset
uspto-grants-2003_07
Patent number
US06593330B2

Reaction notes

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