Chloroform → HCID 70163066, compound

HRID 2185929Notes

Reaction equation

HRID 2185929 reaction equation
C(Cl)(Cl)Cl.[NH2:5][CH2:6][CH2:7][NH:8][C:9]1[CH:14]=[CH:13][C:12]([Cl:15])=[CH:11][CH:10]=1.Cl[C:17]1[C:22]([N+:23]([O-:25])=[O:24])=[CH:21][CH:20]=[CH:19][N:18]=1>C(N(CC)CC)C>[Cl:15][C:12]1[CH:13]=[CH:14][C:9]([NH:8][CH2:7][CH2:6][NH:5][C:17]2[C:22]([N+:23]([O-:25])=[O:24])=[CH:21][CH:20]=[CH:19][N:18]=2)=[CH:10][CH:11]=1

Participants

5

Reactant 3

HCID 6212ChloroformHCID 796132-Chloro-3-nitropyridineHCID 12666393N-(2-Aminoethyl)-N-(4-chlorophenyl)amine

Product 1

HCID 70163066HCID 70163066, compoundYield 97.9%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

Chloroform (1000 ml) was added to N-(2-aminoethyl)-p-chloroaniline (116.67 g) and the mixture was dissolved. Triethylamine (83.02 g) and 2-chloro-3-nitropyridine (108.40 g) were added to the resultant solution on ice in this order and stirred for 2 hours at room temperature. Subsequently, the resultant mixture was refluxed for one hour, cooled, washed with water (500 ml×2), and the aqueous layer was extracted with chloroform (500 ml). The aqueous layer was combined with the chloroform layer, washed with saturated brine, and dehydrated over anhydrous magnesium sulfate. After filtration, the solvent was removed under reduced pressure. The thus-obtained crystalline residue was purified by silica gel chromatography (elution solvent=chloroform:methanol=100:5), to thereby obtain the target compound in the form of colorless crystals (195.97 g).

Workup

  1. dissolutionthe mixture was dissolved
  2. temperaturecooled
  3. washwashed with water (500 ml×2)
  4. extractionthe aqueous layer was extracted with chloroform (500 ml)
  5. washwashed with saturated brine
  6. filtrationAfter filtration
  7. customthe solvent was removed under reduced pressure
  8. customThe thus-obtained crystalline residue was purified by silica gel chromatography (elution solvent=chloroform:methanol=100:5)

Sources & evidence

ORD record
ord-1718268e21344afd85799c28b3358bfb
Source dataset
uspto-grants-2002_06
Patent number
US06403607B1

Reaction notes

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