Ethylene Oxide → HCID 22036247, compound

HRID 1789691Notes

Reaction equation

HRID 1789691 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([OH:8])[CH:5]=[CH:6][CH:7]=1.C1OC1.[O:12]([C:14]([CH3:17])(C)C)[K].[Cl:18][C:19]1[C:24](Cl)=[N:23][CH:22]=[CH:21][N:20]=1>CCN(CC)CC.C(Cl)Cl.O1CCOCC1>[Cl:18][C:19]1[C:24]([O:12][CH2:14][CH2:17][O:8][C:4]2[CH:5]=[CH:6][CH:7]=[C:2]([Br:1])[CH:3]=2)=[N:23][CH:22]=[CH:21][N:20]=1

Participants

8

Reactant 4

HCID 6354Ethylene OxideHCID 115633-BromophenolHCID 785752,3-DichloropyrazineHCID 178418922HCID 178418922, compound

Product 1

HCID 22036247HCID 22036247, compoundYield 75%

Reagents, catalysts & solvents 3

HCID 8471TriethylamineCatalystHCID 6344DichloromethaneSolventHCID 312751,4-DioxaneSolvent2×

Procedure

A mixture of 3-bromophenol (1.73 g, 10.0 mmol), ethylene oxide (0.44 g, 10 mmol). Et3N (3 drops) and dioxane (4 mL) was heated at 100° C. in a sealed tube for 2 d. The solution was cooled in an ice-bath and KO-t-Bu (1.07 g, 9.50 mmol) followed by 2,3-dichloropyrazine (1.34 g, 9 mmol) were added along with dioxane (1 mL). The mixture was stirred at room temperature for 90 min, diluted with CH2Cl2 and filtered. The filtrate was concentrated and the residue was purified by chromatography-on silica gel (gradient: isohexane to 25% EtOAc/isohexane) to give 2.21 g (75%) of the title product as a white solid: mp 57-58° C. Anal. (C12H10BrCIN2O2) C, H, N.

Workup

  1. temperatureThe solution was cooled in an ice-bath
  2. filtrationfiltered
  3. concentrationThe filtrate was concentrated
  4. customthe residue was purified by chromatography-on silica gel (gradient: isohexane to 25% EtOAc/isohexane)

Sources & evidence

ORD record
ord-dbe8f8dd9eac420d90e79e467c6f4854
Source dataset
uspto-grants-2006_07
Patent number
US07071180B2

Reaction notes

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