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

HRID 1839363노트

반응식

HRID 1839363 반응식
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

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 312751,4-Dioxane용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-7bad4197d3134a5ab6c45d18d73b3cf3
출처 데이터셋
uspto-grants-2004_01
특허 번호
US06677352B1

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