Chlorosuccinimide → methyl 4-(4-chloro-1-ethyl-1H-pyrazol-5-yl)-2-furancarboxylate

HRID 2392271Notes

Reaction equation

HRID 2392271 reaction equation
[CH2:1]([N:3]1[C:7]([C:8]2[CH:9]=[C:10]([C:13]([O:15][CH3:16])=[O:14])[O:11][CH:12]=2)=[CH:6][CH:5]=[N:4]1)[CH3:2].C1C(=O)N([Cl:24])C(=O)C1>C1COCC1>[Cl:24][C:6]1[CH:5]=[N:4][N:3]([CH2:1][CH3:2])[C:7]=1[C:8]1[CH:9]=[C:10]([C:13]([O:15][CH3:16])=[O:14])[O:11][CH:12]=1

Participants

4

Reactant 2

HCID 31398ChlorosuccinimideHCID 57826888methyl 4-(1-ethyl-1H-pyrazol-5-yl)-2-furancarboxylate

Product 1

HCID 57826620methyl 4-(4-chloro-1-ethyl-1H-pyrazol-5-yl)-2-furancarboxylateYield 75.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of methyl 4-(1-ethyl-1H-pyrazol-5-yl)-2-furancarboxylate (300 mg, 1.36 mmol) and NCS (218 mg, 1.63 mmol) in THF (5 mL) was heated to 70° C. in a sealed tube. After 5 h, the reaction mixture was concentrated and purified via column chromatography (silica, 10-20% EtOAc/Hexane) affording the title compound (260 mg, 75%) as a white solid: LC-MS (ES) m/z 255 (M+H)+.

Workup

  1. concentrationthe reaction mixture was concentrated
  2. custompurified via column chromatography (silica, 10-20% EtOAc/Hexane)

Sources & evidence

ORD record
ord-4804a4b4bdce4b0497c99e9c63727fd2
Source dataset
uspto-grants-2012_09
Patent number
US08273782B2

Reaction notes

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