Chlorosuccinimide → HCID 57826667, compound

HRID 2392296Notes

Reaction equation

HRID 2392296 reaction equation
[CH2:1]([N:3]1[C:7]([C:8]2[CH:9]=[C:10]([C:14]([O:16][CH3:17])=[O:15])[O:11][C:12]=2[CH3:13])=[CH:6][CH:5]=[N:4]1)[CH3:2].C1C(=O)N([Cl:25])C(=O)C1>C1COCC1>[Cl:25][C:6]1[CH:5]=[N:4][N:3]([CH2:1][CH3:2])[C:7]=1[C:8]1[CH:9]=[C:10]([C:14]([O:16][CH3:17])=[O:15])[O:11][C:12]=1[CH3:13]

Participants

4

Reactant 2

HCID 31398ChlorosuccinimideHCID 57826453methyl 4-(1-ethyl-1H-pyrazol-5-yl)-5-methyl-2-furancarboxylate

Product 1

HCID 57826667HCID 57826667, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of methyl 4-(1-ethyl-1H-pyrazol-5-yl)-5-methyl-2-furancarboxylate (950 mg, 4.06 mmol) and NCS (650 mg, 4.87 mmol) in THF (10 mL) was heated at 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 (970 mg, 89%) as a white solid: LC-MS (ES) m/z 269 (M+H)+.

Workup

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

Sources & evidence

ORD record
ord-96be9b65b3c94480973defe66098bc27
Source dataset
uspto-grants-2012_09
Patent number
US08273782B2

Reaction notes

Loading…