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

HRID 266919Notes

Reaction equation

HRID 266919 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-f78558e151934e1a862942949131d02d
Source dataset
uspto-grants-1997_07
Patent number
US05652366

Reaction notes

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