Aniline → HCID 21948204, compound

HRID 2183774Notes

Reaction equation

HRID 2183774 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl[C:9](Cl)=[CH:10][C:11]([C:13]1[C:14]([Cl:20])=[N:15][C:16]([Cl:19])=[CH:17][CH:18]=1)=[O:12]>O1CCOCC1>[NH:1]([C:9]([NH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)=[CH:10][C:11]([C:13]1[C:14]([Cl:20])=[N:15][C:16]([Cl:19])=[CH:17][CH:18]=1)=[O:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 6115AnilineHCID 21948210HCID 21948210, compound

Product 1

HCID 21948204HCID 21948204, compoundYield 49%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
0 °C

Procedure

A solution of aniline (1.01 mL, 11.1 mmol) in TEA (1.55 mL, 11.1 mmol) was added slowly to a cooled (0° C.) and stirred solution of 3,3-dichloro-1-(2,6-dichloro-3-pyridinyl)-2-propen-1-one (1.0 g, 3.69 mmol) in dioxane (20 mL). The reaction was allowed to warm to room temperature and was stirred overnight. The mixture was concentrated in vacuo until most of the solvent was removed. The residue was diluted with water and extracted with EtOAc (3×). The combined organic extracts were washed with water, dried over Na2SO4 and concentrated in vacuo. Silica gel flash chromatography of the residue using 6:1 EtOAc:Hex gave 3,3-dianilino-1-(2,6-dichloro-3-pyridinyl)-2-propen-1-one as pale yellow solid (0.69 g, 49%): LCMS RT: 3.81 min; MH+: 384.2.

Workup

  1. temperatureto warm to room temperature
  2. concentrationThe mixture was concentrated in vacuo until most of the solvent
  3. customwas removed
  4. additionThe residue was diluted with water
  5. extractionextracted with EtOAc (3×)
  6. washThe combined organic extracts were washed with water
  7. dry with materialdried over Na2SO4
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-25a0546727d94cf1968d1e0c6f503a2f
Source dataset
uspto-grants-2005_05
Patent number
US06900205B2

Reaction notes

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