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

HRID 2392284Notes

Reaction equation

HRID 2392284 reaction equation
[Cl:1][C:2]1[O:6][C:5]([C:7]([O:9][CH3:10])=[O:8])=[CH:4][C:3]=1[C:11]1[N:15]([CH2:16][CH3:17])[N:14]=[CH:13][CH:12]=1.C1C(=O)N([Cl:25])C(=O)C1>C1COCC1>[Cl:1][C:2]1[O:6][C:5]([C:7]([O:9][CH3:10])=[O:8])=[CH:4][C:3]=1[C:11]1[N:15]([CH2:16][CH3:17])[N:14]=[CH:13][C:12]=1[Cl:25]

Participants

4

Reactant 2

HCID 31398ChlorosuccinimideHCID 57826756methyl 5-chloro-4-(1-ethyl-1H-pyrazol-5-yl)-2-furancarboxylate

Product 1

HCID 57826817methyl 5-chloro-4-(4-chloro-1-ethyl-1H-pyrazol-5-yl)-2-furancarboxylateYield 78.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of methyl 5-chloro-4-(1-ethyl-1H-pyrazol-5-yl)-2-furancarboxylate (800 mg, 3.14 mmol) and NCS (600 mg, 4.49 mmol) in THF (5 mL) was heated to 70° C. in a sealed tube. After 2 h, the reaction mixture was concentrated and purified via column chromatography (silica, 10-20% EtOAc/Hexane) affording the title compound (710 mg, 78%) as a white solid: LC-MS (ES) m/z 289 (M+H)+.

Workup

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

Sources & evidence

ORD record
ord-ad1e02a6e9a746ca9437ecde9f3375bf
Source dataset
uspto-grants-2012_09
Patent number
US08273782B2

Reaction notes

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