Aniline → 3,3-Dianilino-1-(2,6-dichloro-5-fluoro-3-pyridinyl)-2-propen-1-one

HRID 1063527Notes

Reaction equation

HRID 1063527 reaction equation
Cl[C:2](Cl)=[CH:3][C:4]([C:6]1[C:7]([Cl:14])=[N:8][C:9]([Cl:13])=[C:10]([F:12])[CH:11]=1)=[O:5].[NH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>O1CCOCC1>[NH:16]([C:2]([NH:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=[CH:3][C:4]([C:6]1[C:7]([Cl:14])=[N:8][C:9]([Cl:13])=[C:10]([F:12])[CH:11]=1)=[O:5])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

4

Reactant 2

HCID 6115AnilineHCID 219481323,3-Dichloro-1-(2,6-dichloro-5-fluoro-3-pyridinyl)-2-propen-1-one

Product 1

HCID 219481383,3-Dianilino-1-(2,6-dichloro-5-fluoro-3-pyridinyl)-2-propen-1-oneYield 49%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a 0° C. solution of 3,3-dichloro-1-(2,6-dichloro-5-fluoro-3-pyridinyl)-2-propen-1-one (6.70 g, 23.2 mmol) in dioxane (50 mL) was added TEA (9.7 mL, 69.6) followed by aniline (6.3 mL, 69.6 mmol). After 1 h 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 and then the residue was diluted with water and extracted with CH2Cl2 (2×). The combined organic extracts were washed with water, dried over Na2SO4 and concentrated in vacuo. Purification of the residue by silica gel Biotage chromatography provided 3,3-dianilino-1-(2,6-dichloro-5-fluoro-3-pyridinyl)-2-propen-1-one as yellow solid (4.2 g, 49%): LCMS RT: 3.47 min; MH+: 402.6.

Workup

  1. concentrationThe mixture was concentrated in vacuo until most of the solvent
  2. customwas removed
  3. additionthe residue was diluted with water
  4. extractionextracted with CH2Cl2 (2×)
  5. washThe combined organic extracts were washed with water
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated in vacuo
  8. customPurification of the residue by silica gel Biotage chromatography

Sources & evidence

ORD record
ord-e060821f92f04033b67caaef11f85163
Source dataset
uspto-grants-2005_11
Patent number
US06964971B2

Reaction notes

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