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

HRID 863777Notes

Reaction equation

HRID 863777 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-e722668d275d4ca6ac5ae4c1c13ec5a1
Source dataset
uspto-grants-1996_10
Patent number
US05561134

Reaction notes

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