Ethylene Oxide → HCID 22036247, compound

HRID 493276Notes

Reaction equation

HRID 493276 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×

Conditions

Temperature
100 °C

Procedure

A mixture of 3-bromophenol (173 g. 100 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. (C12H10BrClN2O2) 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-412e29f45fac4f7a832b7fff08d59d45
Source dataset
uspto-grants-2009_05
Patent number
US07534794B2

Reaction notes

Loading…