Potassium Iodide → HCID 65807613, compound

HRID 929917Notes

Reaction equation

HRID 929917 reaction equation
Cl[CH2:2][C:3]([NH:5][C@@H:6]([CH3:9])[CH2:7][OH:8])=[O:4].[I-].[K+].C(=O)([O-])[O-].[Cs+].[Cs+].[N+:18]([C:21]1[CH:22]=[N:23][NH:24][CH:25]=1)([O-:20])=[O:19]>C(#N)C.O>[OH:8][CH2:7][C@@H:6]([NH:5][C:3](=[O:4])[CH2:2][N:23]1[CH:22]=[C:21]([N+:18]([O-:20])=[O:19])[CH:25]=[N:24]1)[CH3:9]

Participants

7

Reactant 4

HCID 4875Potassium IodideHCID 10796Cesium carbonateHCID 163764-nitro-1H-pyrazoleHCID 12032304HCID 12032304, compound

Product 1

HCID 65807613HCID 65807613, compoundYield 896.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Conditions

Temperature
160 °C

Procedure

2-Chloro-N—((S)-1-hydroxypropan-2-yl)acetamide (700 mg, 4.64 mmol), potassium iodide (960 mg, 5.8 mmol) and cesium carbonate (1.9 g, 5.8 mmol) were added to a solution of 4-nitropyrazole (436 mg, 3.86 mmol) in acetonitrile (10 mL) then the mixture was heated to 160° C. for 30 min in a microwave reactor. The reaction mixture was combined with those from 13 other identical reactions, diluted with water then extracted four times with ethyl acetate. The combined organic layers were dried, concentrated in vacuo and purified by column chromatography (3% v/v MeOH/DCM) to afford (S)—N-(1-hydroxypropan-2-yl)-2-(4-nitro-1H-pyrazol-1-yl)acetamide (7.9 g, 64%) as a white solid.

Workup

  1. extractionthen extracted four times with ethyl acetate
  2. customThe combined organic layers were dried
  3. concentrationconcentrated in vacuo
  4. custompurified by column chromatography (3% v/v MeOH/DCM)

Sources & evidence

ORD record
ord-9a30e8ac1bf240a3b438a6ce728cee41
Source dataset
uspto-grants-2016_03
Patent number
US09296725B2

Reaction notes

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