Triethylamine → 4-[(4-Nitrophthalimido)methylthio]pyridine

HRID 6146Notes

Reaction equation

HRID 6146 reaction equation
Cl[CH2:2][N:3]1[C:7](=[O:8])[C:6]2=[CH:9][C:10]([N+:13]([O-:15])=[O:14])=[CH:11][CH:12]=[C:5]2[C:4]1=[O:16].[SH:17][C:18]1[CH:23]=[CH:22][N:21]=[CH:20][CH:19]=1.C(N(CC)CC)C>C(O)C>[N+:13]([C:10]1[CH:9]=[C:6]2[C:7](=[O:8])[N:3]([CH2:2][S:17][C:18]3[CH:23]=[CH:22][N:21]=[CH:20][CH:19]=3)[C:4](=[O:16])[C:5]2=[CH:12][CH:11]=1)([O-:15])=[O:14]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 3016883N-Chloromethyl-4-nitrophthalimide [for HPLC Labeling]HCID 178418431pyridine-4-thiol

Product 1

HCID 190791754-[(4-Nitrophthalimido)methylthio]pyridineYield 63.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

N-Chloromethyl-4-nitrophthalimide [2.89 g (12 mmol)] was added under ice-cooling with stirring to a suspension of 1.11 g (10 mmol) of 4-mercaptopyridine and 1.4 ml (12 mmol) of triethylamine in 50 ml of ethanol. The mixture was stirred at room temperature for 16 hours. The solvent was distilled off and the residue was purified by column chromatography (eluent: ethyl acetate) to obtain 1.99 g of the desired compound (yield: 63.1%, yellow crystals).

Workup

  1. temperaturecooling
  2. distillationThe solvent was distilled off
  3. customthe residue was purified by column chromatography (eluent: ethyl acetate)

Sources & evidence

ORD record
ord-c02e45927e744116961d5f80a7284f40
Source dataset
uspto-grants-1993_09
Patent number
US05246948

Reaction notes

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