Chlorosuccinimide → (4-chloro-5-methyl-1H-pyrazol-1-yl)acetic acid
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
Product 1
Reagents, catalysts & solvents 1
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
- temperatureIt was then cooled to rt
- customevaporated in vacuo
- custompurified by flash chromatography (SiO2
- 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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