Ethylenediamine → HCID 58333161, compound

HRID 2405073Notes

Reaction equation

HRID 2405073 reaction equation
[Cl:1][C:2]1[C:16]([Cl:17])=[CH:15][C:5]2[NH:6][C:7]([C:9](=O)[C:10]([F:13])([F:12])[F:11])=[N:8][C:4]=2[CH:3]=1.[CH2:18]([NH2:21])[CH2:19][NH2:20].O.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[Cl:1][C:2]1[C:16]([Cl:17])=[CH:15][C:5]2[NH:6][C:7]([C:9]3([C:10]([F:13])([F:12])[F:11])[NH:21][CH2:18][CH2:19][NH:20]3)=[N:8][C:4]=2[CH:3]=1

Participants

5

Reactant 3

HCID 3301Ethylenediamine2×HCID 521998p-Toluenesulfonic acid monohydrateHCID 115943701-(5,6-dichloro-1H-benzoimidazol-2-yl)-2,2,2-trifluoro-ethanone

Product 1

HCID 58333161HCID 58333161, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

1-(5,6-DiChloro-1H-benzoimidazol-2-yl)-2,2,2-trifluoro-ethanone (1.02 g; 3.61 mmol), ethylene diamine (0.74 mL; 11.04 mmol) and para-toluenesulphonic acid monohydrate (0.12 g; 0.603 mmol) were suspended in toluene (80 mL), then heated to reflux with a Dean-Stark trap for 3 hrs. After 3 hrs, ethylene diamine (0.74 mL; 11.04 mmol) was added to the reaction mixture and the reaction mixture was allowed to reflux with the Dean-Stark trap for 18 hrs. The reaction was cooled to room temperature and concentrated in vacuo to a crude brown residue. The crude brown residue was dissolved in ethyl acetate (60 mL), washed with water (3×50 mL) and brine (50 mL), then dried over Na2SO4. The drying agent was removed by filtration and the filtrate was concentrated in vacuo to a crude brown oil, which was purified by column chromatography (SiO2, 50% ethyl acetate/hexanes) to yield the title compound as a light orange solid.

Workup

  1. temperatureheated
  2. temperatureto reflux with a Dean-Stark trap for 3 hrs
  3. temperatureto reflux with the Dean-Stark trap for 18 hrs
  4. concentrationconcentrated in vacuo to a crude brown residue
  5. dissolutionThe crude brown residue was dissolved in ethyl acetate (60 mL)
  6. washwashed with water (3×50 mL) and brine (50 mL)
  7. dry with materialdried over Na2SO4
  8. customThe drying agent was removed by filtration
  9. concentrationthe filtrate was concentrated in vacuo to a crude brown oil, which
  10. customwas purified by column chromatography (SiO2, 50% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-228bb01e88634e03b58a6b7db79802f9
Source dataset
uspto-grants-2014_08
Patent number
US08802865B2

Reaction notes

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