Chlorosuccinimide → Methyl 5-chloro-4-(4-chloro-1-ethyl-1H-pyrazol-5-yl)-2-thiophenecarboxylate

HRID 2392282Notes

Reaction equation

HRID 2392282 reaction equation
[Cl:1][C:2]1[S: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[S: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 57826590Methyl 5-chloro-4-(1-ethyl-1H-pyrazol-5-yl)-2-thiophenecarboxylate

Product 1

HCID 57826495Methyl 5-chloro-4-(4-chloro-1-ethyl-1H-pyrazol-5-yl)-2-thiophenecarboxylateYield 74%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Methyl 5-chloro-4-(1-ethyl-1H-pyrazol-5-yl)-2-thiophenecarboxylate (1.8 g, 6.65 mmol) and NCS (1.3 g, 9.74 mmol) in THF (10 mL) were heated to 70° C. under N2 for 2 h. The reaction solution was concentrated and purified on silica (EtOAc/Hex, 10-30%) to afford the title compound (1.5 g, 74%) as a syrup: LC-MS (ES) m/z 305 (M+H)+.

Workup

  1. concentrationThe reaction solution was concentrated
  2. custompurified on silica (EtOAc/Hex, 10-30%)

Sources & evidence

ORD record
ord-c66fdac1df5c441da3327651848279f6
Source dataset
uspto-grants-2012_09
Patent number
US08273782B2

Reaction notes

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