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

HRID 2214990ノート

反応式

HRID 2214990 の反応式
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

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 312751,4-Dioxane溶媒

実験手順

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 I 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.

後処理

  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

出典と根拠

ORDレコード
ord-f7194b3ad63a49358506c0b6b51b6b6f
出典データセット
uspto-grants-2006_09
特許番号
US07109196B2

反応ノート

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