Cesium carbonate → HCID 60886989, compound

HRID 522663Notes

Reaction equation

HRID 522663 reaction equation
[N+:1]([C:4]1[CH:5]=[N:6][NH:7][CH:8]=1)([O-:3])=[O:2].Cl[CH2:10][C:11]([CH3:14])([OH:13])[CH3:12].C([O-])([O-])=O.[Cs+].[Cs+]>CN(C=O)C.CC(=O)OCC>[CH3:10][C:11]([OH:13])([CH3:14])[CH2:12][N:6]1[CH:5]=[C:4]([N+:1]([O-:3])=[O:2])[CH:8]=[N:7]1

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 163764-nitro-1H-pyrazoleHCID 684091-Chloro-2-methylpropan-2-ol

Product 1

HCID 60886989HCID 60886989, compoundYield 78%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 4-nitro-1H-pyrazole (1.6 g, 13.9 mmol), 1-chloro-2-methylpropan-2-ol (1.5 g, 13.9 mmol) and Cs2CO3 (9.1 g, 27.8 mmol) in DMF (20 mL) was stirred at 80° C. for 5 h. The reaction mixture was cooled to RT and diluted with EA (200 ml). The organic phase was washed by water (50 mL) and brine (50 mL), dried over anhydrous sodium sulfate and concentrated under reduced pressure to give 2-methyl-1-(4-nitro-1H-pyrazol-1-yl)propan-2-ol as a yellow oil (2.0 g, 78%), which was used for the next step without further purification. MS (ES+) C7H11N3O3 requires: 185, found: 186 [M+H]+.

Workup

  1. temperatureThe reaction mixture was cooled to RT
  2. washThe organic phase was washed by water (50 mL) and brine (50 mL)
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-05aefa342c2242658f8f626eec868889
Source dataset
uspto-grants-2016_05
Patent number
US09334263B2

Reaction notes

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