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

HRID 1845650Notes

Reaction equation

HRID 1845650 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](/[N:14]([CH2:17][CH3:18])[N:15]=[CH2:16])=[CH:12]/C.[Cl:19]N1C(=O)CCC1=O>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:14]([CH2:17][CH3:18])[N:15]=[CH:16][C:12]=1[Cl:19]

Participants

4

Reactant 2

HCID 31398ChlorosuccinimideHCID 68670418Methyl 5-chloro-4-[(1Z)-1-(1-ethyl-2-methylidenehydrazino)-1-propen-1-yl]-2-thiophenecarboxylate

Product 1

HCID 57826495Methyl 5-chloro-4-(4-chloro-1-ethyl-1H-pyrazol-5-yl)-2-thiophenecarboxylateYield 95.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Methyl 5-chloro-4-[(1Z)-1-(1-ethyl-2-methylidenehydrazino)-1-propen-1-yl]-2-thiophenecarboxylate (260 mg, 0.96 mmol) and 1-chloro-2,5-pyrrolidinedione (154 mg, 1.15 mmol) in THF (4 mL) were heated at 70° C. under N2 for 2 h, concentrated and purified on silica (EtOAc/Hex, 10-30%) to afford the title compound (0.281 g, 83%) as a syrup: LC-MS (ES) m/z=305 (M+H)+.

Workup

  1. concentrationconcentrated
  2. custompurified on silica (EtOAc/Hex, 10-30%)

Sources & evidence

ORD record
ord-e9397904159147669d9ee75f96efd00c
Source dataset
uspto-grants-2015_02
Patent number
US08946278B2

Reaction notes

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