Triethylamine → 2-Chloro-3-nitro-4-[2-(2-thiophenyl)ethyl]aminopyridine

HRID 381686Notes

Reaction equation

HRID 381686 reaction equation
[Cl:1][C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[C:6](Cl)[CH:5]=[CH:4][N:3]=1.[NH2:12][CH2:13][CH2:14][C:15]1[S:16][CH:17]=[CH:18][CH:19]=1.C(N(CC)CC)C>CCO>[Cl:1][C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[C:6]([NH:12][CH2:13][CH2:14][C:15]2[S:16][CH:17]=[CH:18][CH:19]=2)[CH:5]=[CH:4][N:3]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 116521ThiopheneethanamineHCID 105357732,4-Dichloro-3-nitropyridine

Product 1

HCID 224633192-Chloro-3-nitro-4-[2-(2-thiophenyl)ethyl]aminopyridine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 2,4-dichloro-3-nitropyridine (1.5 g), 2-aminoethylthiophene (1 g) and triethylamine (5 mL) is heated to reflux in EtOH (60 mL). The reaction mixture is cooled, the solvent evaporated and the residue chromatographed on silica gel (10% hexane/CH2Cl2) to yield the desired addition product.

Workup

  1. temperatureis heated
  2. temperatureThe reaction mixture is cooled
  3. customthe solvent evaporated
  4. customthe residue chromatographed on silica gel (10% hexane/CH2Cl2)
  5. customto yield the desired
  6. additionaddition product

Sources & evidence

ORD record
ord-1a18771d1d37401db6fc677a7f88697a
Source dataset
uspto-grants-2001_10
Patent number
US06307054B1

Reaction notes

Loading…