Water → HCID 18009342, compound

HRID 2229905Notes

Reaction equation

HRID 2229905 reaction equation
C[C:2]1[CH:8]=[C:7]([CH3:9])[CH:6]=C[C:3]=1[NH2:4].BrN1C(=O)CC[C:12]1=O.O.[CH2:19]([NH2:22])[CH2:20]N>ClCCl>[C:3]([C:2]1[CH:8]=[C:7]([CH3:9])[CH:6]=[C:20]([CH3:12])[C:19]=1[NH2:22])#[N:4]

Participants

6

Reactant 4

HCID 962WaterHCID 3301EthylenediamineHCID 72502,4-DimethylanilineHCID 67184N-bromobutanimide

Product 1

HCID 18009342HCID 18009342, compoundYield 55%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2,4-dimethylaniline (9.80 g, 80.9 mmol) in dichloromethane (200 mL) at 0° C. was added N-bromosuccinimide (15.1 g, 84.9 mmol) slowly. The mixture was allowed to warmed to room temperature and stirred at room temperature overnight before it was washed with 1 N NaOH. The organic layer was worked up and concentrated as usual. The residue was dissolved in N,N-dimethylformamide (120 mL) followed by the addition of cuprous cyanide (14.5 g, 161.8 mmol). The mixture was heated under reflux for 8 h and then allowed to cool to rt and poured into water (1 L). The mixture was treated with excess ethylenediamine and the precipitate was filtered, redissolved in ethyl acetate, dried with MgSO4 and then concentrated to give the desired compound as an oil (6.7 g, 55%).

Workup

  1. washwas washed with 1 N NaOH
  2. concentrationconcentrated as usual
  3. dissolutionThe residue was dissolved in N,N-dimethylformamide (120 mL)
  4. temperatureThe mixture was heated
  5. temperatureunder reflux for 8 h
  6. temperatureto cool to rt
  7. filtrationthe precipitate was filtered
  8. dissolutionredissolved in ethyl acetate
  9. dry with materialdried with MgSO4
  10. concentrationconcentrated

Sources & evidence

ORD record
ord-a83c284694274204a35307654a574ed3
Source dataset
uspto-grants-2002_07
Patent number
US06420567B1

Reaction notes

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