Dimethylformamide → 3-Chloro-N-(3-chloropropyl)-4-methylaniline

HRID 412872Notes

Reaction equation

HRID 412872 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:6]=[CH:7][C:8]=1[CH3:9])[NH2:5].[Cl:10][CH2:11][CH2:12][CH2:13]I.C(=O)([O-])[O-].[Cs+].[Cs+].CN(C=O)C>O>[Cl:1][C:2]1[CH:3]=[C:4]([CH:6]=[CH:7][C:8]=1[CH3:9])[NH:5][CH2:13][CH2:12][CH2:11][Cl:10]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 72553-Chloro-4-methylanilineHCID 10796Cesium carbonateHCID 813631-Chloro-3-iodopropane

Product 1

HCID 117015893-Chloro-N-(3-chloropropyl)-4-methylanilineYield 61%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 3-chloro-4-methylaniline (7.79 g, 55 mmol), 1-chloro-3-iodopropane (5.91 ml, 55 mmol), cesium carbonate (35.84 g, 110 mmol) and DMF (15 ml) was stirred at room temperature for 19 hours. To the mixture was added water (75 ml), and the mixture was extracted with hexane (60 ml, 30 ml×2). The organic layer was washed with water (10 ml), dried over magnesium sulfate and concentrated under reduced pressure. The concentrate was subjected to column chromatography (silica gel 200 g, hexane/ethyl acetate=1/0 to 19/1), and the desired fraction was concentrated under reduced pressure to give the titled compound (7.30 g, 33 mmol, Yield 61%) as a pale brown oily substance.

Workup

  1. extractionthe mixture was extracted with hexane (60 ml, 30 ml×2)
  2. washThe organic layer was washed with water (10 ml)
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. concentrationthe desired fraction was concentrated under reduced pressure

Sources & evidence

ORD record
ord-a575456d03614ecb8c839cb8963af4fc
Source dataset
uspto-grants-2003_05
Patent number
US06562978B1

Reaction notes

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