Water → HCID 22097093, compound

HRID 861534Notes

Reaction equation

HRID 861534 reaction equation
Cl[C:2]1[CH:7]=[CH:6][C:5]([Cl:8])=[CH:4][C:3]=1[N+:9]([O-:11])=[O:10].[CH3:12][C:13]([CH3:17])([CH3:16])[CH2:14][NH2:15].C(=O)([O-])[O-].[K+].[K+].O>CN(C)C=O.[I-].[Na+]>[Cl:8][C:5]1[CH:6]=[CH:7][C:2]([NH:15][CH2:14][C:13]([CH3:17])([CH3:16])[CH3:12])=[C:3]([N+:9]([O-:11])=[O:10])[CH:4]=1

Participants

7

Reactant 4

HCID 962WaterHCID 69772,5-DichloronitrobenzeneHCID 11430Potassium CarbonateHCID 79882Neopentylamine

Product 1

HCID 22097093HCID 22097093, compoundYield 50%

Reagents, catalysts & solvents 2

HCID 5238Sodium IodideCatalystHCID 6228DimethylformamideSolvent

Procedure

57.6 g (0.3 mol) of 2,5-dichloronitrobenzene, 26.2 g (0.3 mol) of 2,2-dimethylpropylamine, 82.9 g (0.6 mol) of potassium carbonate and 0.5 g of sodium iodide in 400 ml of dimethylformamide were heated at 80° C. for 10 h. The mixture was then added to a large amount of water and extracted with ethyl acetate. The organic phase was dried and concentrated under reduced pressure. The residue was purified by chromatography on silica gel (mobile phase: petroleum ether/toluene=16/1) to yield 32.3 g (50%) of the product. Melting point 78° C.

Workup

  1. extractionextracted with ethyl acetate
  2. customThe organic phase was dried
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by chromatography on silica gel (mobile phase: petroleum ether/toluene=16/1)

Sources & evidence

ORD record
ord-71afd31c09334f03938b25f4f1b1c17f
Source dataset
uspto-grants-1998_02
Patent number
US05714489

Reaction notes

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