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

HRID 1598007Notes

Reaction equation

HRID 1598007 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-be941b8a310d440ba6886c6345d66488
Source dataset
uspto-grants-1998_04
Patent number
US05736554

Reaction notes

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