Benzyl Alcohol → 5-benzyloxy-N-methyl-2-nitroaniline

HRID 1430400노트

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HRID 1430400 반응식
[CH2:1]([OH:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].C1(C)C=CC=CC=1.F[C:23]1[CH:24]=[CH:25][C:26]([N+:31]([O-:33])=[O:32])=[C:27]([CH:30]=1)[NH:28][CH3:29]>[Cl-].C([N+](CCCC)(CCCC)CCCC)CCC.O>[CH2:1]([O:8][C:23]1[CH:24]=[CH:25][C:26]([N+:31]([O-:33])=[O:32])=[C:27]([CH:30]=1)[NH:28][CH3:29])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

참가 물질

7

반응물 4

HCID 244Benzyl AlcoholHCID 1140TolueneHCID 11430Potassium CarbonateHCID 229057745-fluoro-N-methyl-2-nitroaniline

생성물 1

HCID 679540515-benzyloxy-N-methyl-2-nitroaniline수율 92%

시약·촉매·용매 2

HCID 70681Tetrabutylammonium Chloride촉매HCID 962Water용매

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온도
65 °C

실험 절차

Benzyl alcohol (49.6 mL, 0.48 mol), tetrabutyl ammonium chloride (6.66 g, 24.0 mmol) and potassium carbonate (40.0 g, 0.29 mol) were added to a toluene solution (200 mL) of 5-fluoro-N-methyl-2-nitroaniline (40.8 g, 0.24 mol), and the mixture was heated under reflux for 3.5 hours. The reaction solution was cooled, and 100 mL of water was added thereto. Thereafter, the mixture was stirred for 1 hour at 60 to 70° C. After the mixture was stirred under ice cooling for 30 minutes, precipitated crystals were collected by filtration. The resulting crystals were washed with water, and dried at 50° C., thereby obtaining 57.1 g of an orange, powdery target compound (yield: 92%).

후처리

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 3.5 hours
  3. temperatureThe reaction solution was cooled
  4. stirringAfter the mixture was stirred under ice cooling for 30 minutes
  5. customprecipitated crystals
  6. filtrationwere collected by filtration
  7. washThe resulting crystals were washed with water
  8. customdried at 50° C.

출처 및 근거

ORD 기록
ord-5b196df8704a4b269a2393375eb08724
출처 데이터셋
uspto-grants-2015_01
특허 번호
US08940889B2

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