Water → 4-Chloro-2,6-diisopropylaniline

HRID 2303586Notes

Reaction equation

HRID 2303586 reaction equation
[CH:1]([C:4]1[CH:10]=[CH:9][CH:8]=[C:7]([CH:11]([CH3:13])[CH3:12])[C:5]=1[NH2:6])([CH3:3])[CH3:2].[Cl:14]N1C(=O)CCC1=O.O>CN(C)C=O>[Cl:14][C:9]1[CH:10]=[C:4]([CH:1]([CH3:3])[CH3:2])[C:5]([NH2:6])=[C:7]([CH:11]([CH3:13])[CH3:12])[CH:8]=1

Participants

5

Reactant 3

HCID 962WaterHCID 31398ChlorosuccinimideHCID 32484Diisopropylaniline

Product 1

HCID 108891984-Chloro-2,6-diisopropylanilineYield 57%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of 2,6-diisopropylaniline (47 grams) in N,N-dimethylformamide (886 mL) was added N-chlorosuccinimide (37.3 grams) and the mixture was stirred overnight. The resulting dark red solution was poured into water (12 L) and extracted with diethyl ether. The combined ether extracts were washed with water and brine, dried over anhydrous sodium sulfate and concentrated in vacuo. The resulting dark red oil was purified by filtration through silica gel, eluting with 6:1 hexane/methylene chloride to afford 32 grams of the title compound. 1H NMR δ 7.02 (s, 2), 3.71 (br s, 2), 2.91 (qq, 2, J=6.9 Hz), 1.27 (d, 6, J=6.9 Hz), 6.9 Hz).

Workup

  1. extractionextracted with diethyl ether
  2. washThe combined ether extracts were washed with water and brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated in vacuo
  5. filtrationThe resulting dark red oil was purified by filtration through silica gel
  6. washeluting with 6:1 hexane/methylene chloride

Sources & evidence

ORD record
ord-2616feb38c9145198114c7c8f15c2cb7
Source dataset
uspto-grants-2002_08
Patent number
US06433009B1

Reaction notes

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