Isobutylene oxide → HCID 60886989, compound

HRID 1487643Notes

Reaction equation

HRID 1487643 reaction equation
[N+:1]([C:4]1[CH:5]=[N:6][NH:7][CH:8]=1)([O-:3])=[O:2].N1(C2CCCCCCCCCC2)CCCN=CCCCCC1.[O:31]1[C:33]([CH3:35])([CH3:34])[CH2:32]1>C(#N)C>[CH3:32][C:33]([OH:31])([CH3:35])[CH2:34][N:6]1[CH:5]=[C:4]([N+:1]([O-:3])=[O:2])[CH:8]=[N:7]1

Participants

5

Reactant 3

HCID 11208Isobutylene oxideHCID 163764-nitro-1H-pyrazoleHCID 1296629601,8-Diazabicycloundec-7ene

Product 1

HCID 60886989HCID 60886989, compoundYield 73%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 4-nitro-1H-pyrazole (1 equiv) in acetonitrile (1 M) was added 1,8-diazabicycloundec-7ene (2 equiv) and 1,2-epoxy-2-methylpropane (3.2 equiv). The reaction mixture was stirred at 60° C. for 20 h. The solvent was removed under reduced pressure and the residue was dissolved in ethyl acetate. The organic solution was washed with HCl (1 N), water and brine, dried over anhydrous sodium sulfate, filtered and concentrated in vacuo to give the title compound which was directly used in the next step without further purification (73% yield). 1H NMR (400 MHz, CHLOROFORM-d1) δ ppm 8.26 (s, 1H), 8.09 (s, 1H), 4.13 (s, 2H), 2.64 (s, 1H) 1.24 (s, 6H). MS (ESI) m/z 186.2 [M+H]+.

Workup

  1. customThe solvent was removed under reduced pressure
  2. dissolutionthe residue was dissolved in ethyl acetate
  3. washThe organic solution was washed with HCl (1 N), water and brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-9ee7837648134630be39c6d959c7a0b9
Source dataset
uspto-grants-2016_08
Patent number
US09428509B2

Reaction notes

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