Chlorosuccinimide → 4-Chloro-5-methyl-1H-pyrazole-1-acetic acid

HRID 710652Notes

Reaction equation

HRID 710652 reaction equation
[CH3:1][C:2]1[N:6]([CH2:7][C:8]([OH:10])=[O:9])[N:5]=[CH:4][CH:3]=1.C1C(=O)N([Cl:18])C(=O)C1>CC#N>[Cl:18][C:3]1[CH:4]=[N:5][N:6]([CH2:7][C:8]([OH:10])=[O:9])[C:2]=1[CH3:1]

Participants

4

Reactant 2

HCID 31398ChlorosuccinimideHCID 7018400(5-methyl-1H-pyrazol-1-yl)acetic acid

Product 1

HCID 70184024-Chloro-5-methyl-1H-pyrazole-1-acetic acidYield 100%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 2-(5-methylpyrazol-1-yl)acetic acid (0.700 g, 5 mmol) and NCS (0.668 g, 5 mmol) in CH3CN (10 mL) was heated at 80° C. for 1.5 hrs. It was then cooled to rt, evaporated in vacuo, and purified by flash chromatography (SiO2, with a gradient elution of 0-20% MeOH/CH2Cl2) to afford 2-(4-chloro-5-methylpyrazol-1-yl)acetic acid (0.870 g, 100%).

Workup

  1. temperatureIt was then cooled to rt
  2. customevaporated in vacuo
  3. custompurified by flash chromatography (SiO2
  4. washwith a gradient elution of 0-20% MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-ee7fde86b7ae4cdf8487ad0c7d4a9450
Source dataset
uspto-grants-2015_11
Patent number
US09181241B2

Reaction notes

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