Imidazole → HCID 86726478, compound

HRID 1487644Notes

Reaction equation

HRID 1487644 reaction equation
[CH3:1][C:2]([OH:13])([CH3:12])[CH2:3][N:4]1[CH:8]=[C:7]([N+:9]([O-:11])=[O:10])[CH:6]=[N:5]1.[CH3:14][Si:15](Cl)([CH3:17])[CH3:16].N1C=CN=C1>CN(C=O)C.C(OCC)(=O)C>[CH3:12][C:2]([O:13][Si:15]([CH3:17])([CH3:16])[CH3:14])([CH3:1])[CH2:3][N:4]1[CH:8]=[C:7]([N+:9]([O-:11])=[O:10])[CH:6]=[N:5]1

Participants

6

Reactant 3

HCID 795ImidazoleHCID 6397ChlorotrimethylsilaneHCID 60886989HCID 60886989, compound

Product 1

HCID 86726478HCID 86726478, compoundYield 75.5%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 2-methyl-1-(4-nitro-1H-pyrazol-1-yl)propan-2-ol (1 equiv) in dry DMF (0.18 M) was added trimethylsilyl chloride (1.26 equiv) at 0° C. and imidazole (2.55 equiv) under an atmosphere of nitrogen. The resulting mixture was stirred at room temperature for 4 h and then diluted with ethyl acetate. The organic solution was washed with water and brine, dried over sodium sulfate and concentrated under reduced pressure to afford the title compound as a yellow oil (75.5% yield). 1H NMR (400 MHz, CHLOROFORM-d1) δ ppm (9.06 (bs, 1H), 7.91 (s, 1H), 4.13 (s, 3H), 3.79 (s, 2H), 1.70 (s, 9H), 1.68 (s, 6H). MS (ESI) m/z 258.1 [M+H]+.

Workup

  1. washThe organic solution was washed with water and brine
  2. dry with materialdried over sodium sulfate
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-2c721aefcf03487a8427180054be2f68
Source dataset
uspto-grants-2016_08
Patent number
US09428509B2

Reaction notes

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