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Chloroacetyl chloride → N-(2',3',4',6'-tetrafluorophenyl)-N-chloroacetyl-4-methylaniline

HRID 603340
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HRID 603340 반응식
[F:1][C:2]1[C:7]([F:8])=[C:6]([F:9])[CH:5]=[C:4]([F:10])[C:3]=1[NH:11][C:12]1[CH:17]=[CH:16][C:15]([CH3:18])=[CH:14][CH:13]=1.[Cl:19][CH2:20][C:21](Cl)=[O:22]>>[F:1][C:2]1[C:7]([F:8])=[C:6]([F:9])[CH:5]=[C:4]([F:10])[C:3]=1[N:11]([C:21](=[O:22])[CH2:20][Cl:19])[C:12]1[CH:17]=[CH:16][C:15]([CH3:18])=[CH:14][CH:13]=1
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참가 물질

3

반응물 2

HCID 6577Chloroacetyl chlorideHCID 579521482,3,4,6-Tetrafluoro-N-(4-methylphenyl)benzenamine

생성물 1

HCID 57952153N-(2',3',4',6'-tetrafluorophenyl)-N-chloroacetyl-4-methylaniline수율 92.2%

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온도
90 °C

실험 절차

The mixture of N-(2′,3′,4′6′-tetrafluorophenyl)-4-methylanilin (0.82 g, 3.2 mmol) and chloro acetylchloride (1.6 g) is heated with stirring to 90° C. under nitrogen for 1.3 h. To destroy excess of the acid chloride, 2-propanol and water (2 ml each) is added and stirring is continued over night at room temperature. After adding toluene (20 ml), the mixture is extracted with sodium bicarbonate and the organic phase is dried with magnesium sulfate and evaporated to dryness. The residue is purified by flash chromatography (silica, toulene) to obtain N-(2′,3′,4′,6′-tetrafluorophenyl)-N-chloroacetyl-4-methylaniline (0.98 g, 2.95 mmol) as an oil.

후처리

  1. temperatureis heated
  2. customTo destroy excess of the acid chloride, 2-propanol and water (2 ml each)
  3. additionis added
  4. stirringstirring
  5. waitis continued over night at room temperature
  6. additionAfter adding toluene (20 ml)
  7. extractionthe mixture is extracted with sodium bicarbonate
  8. dry with materialthe organic phase is dried with magnesium sulfate
  9. customevaporated to dryness
  10. customThe residue is purified by flash chromatography (silica, toulene)

출처 및 근거

ORD 기록
ord-01a3f40045bc4e8e80d7a2f024dcea47
출처 데이터셋
uspto-grants-2011_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07906677B2

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