Cesium carbonate → HCID 85968314, compound

HRID 522640Notes

Reaction equation

HRID 522640 reaction equation
CC1C=CC(S(O[CH2:12][CH:13]2[CH2:17][O:16][C:15]([CH3:19])([CH3:18])[O:14]2)(=O)=O)=CC=1.[N+:20]([C:23]1[CH:24]=[N:25][NH:26][CH:27]=1)([O-:22])=[O:21].C(=O)([O-])[O-].[Cs+].[Cs+]>C(#N)C>[CH3:19][C:15]1([CH3:18])[O:14][CH:13]([CH2:12][N:25]2[CH:24]=[C:23]([N+:20]([O-:22])=[O:21])[CH:27]=[N:26]2)[CH2:17][O:16]1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 163764-nitro-1H-pyrazoleHCID 2350972,2-Dimethyl-1,3-dioxolan-4-ylmethyl p-toluenesulfonate

Product 1

HCID 85968314HCID 85968314, compoundYield 88.9%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of (2,2-dimethyl-1,3-dioxolan-4-yl)methyl 4-methylbenzenesulfonate (1.57 g, 5.5 mmol), 4-nitro-1H-pyrazole (0.57 g, 5.0 mmol) and cesium carbonate (4.89 g, 15.0 mmol) in acetonitrile (30 mL) was stirred at 70° C. under N2 overnight. The reaction mixture was filtered, and the resulting filtrate was concentrated. The residue was diluted with ethyl acetate (50 mL), washed with water (50 mL×2) and brine (50 mL), dried over sodium sulfate, filtered, and concentrated to afford 1-((2,2-dimethyl-1,3-dioxolan-4-yl)methyl)-4-nitro-1H-pyrazole (1.01 g, crude), which was directly used in the next step without further purification. MS (ES+) C9H13N3O4 requires: 227, found: 228 [M+H]+.

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationthe resulting filtrate was concentrated
  3. additionThe residue was diluted with ethyl acetate (50 mL)
  4. washwashed with water (50 mL×2) and brine (50 mL)
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-705035faee5744e1a7c1e397102c5917
Source dataset
uspto-grants-2016_05
Patent number
US09334263B2

Reaction notes

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