Chlorosuccinimide → HCID 57826858, compound

HRID 1845683Notes

Reaction equation

HRID 1845683 reaction equation
[CH2:1]([N:4]1[C:8]([C:9]2[CH:10]=[C:11]([C:14]([O:16][CH3:17])=[O:15])[S:12][CH:13]=2)=[CH:7][CH:6]=[N:5]1)[CH2:2][CH3:3].C1C(=O)N([Cl:25])C(=O)C1>C1COCC1>[Cl:25][C:7]1[CH:6]=[N:5][N:4]([CH2:1][CH2:2][CH3:3])[C:8]=1[C:9]1[CH:10]=[C:11]([C:14]([O:16][CH3:17])=[O:15])[S:12][CH:13]=1

Participants

4

Reactant 2

HCID 31398ChlorosuccinimideHCID 57826815HCID 57826815, compound

Product 1

HCID 57826858HCID 57826858, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of methyl 4-(1-propyl-1H-pyrazol-5-yl)-2-thiophenecarboxylate (250 mg, 1.0 mmol) and NCS (200 mg, 1.5 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% EtOAc/Hexane) affording the title compound (199 mg, 70%) as a white solid: LC-MS (ES) m/z 285 (M+H)+.

Workup

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

Sources & evidence

ORD record
ord-3d26268d272c43c18116966e9300848f
Source dataset
uspto-grants-2015_02
Patent number
US08946278B2

Reaction notes

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