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Isopropyl Acetate → N-(2,3-dihydro-1H-inden-2-yl)-2,2,2-trifluoroacetamide

HRID 585803
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HRID 585803 반응식
[NH2:1][CH:2]1[CH2:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3]1.C(OC(C)C)(=O)C.[F:18][C:19]([F:26])([F:25])[C:20](OCC)=[O:21]>CCCCCCC>[CH2:3]1[C:4]2[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=2)[CH2:10][CH:2]1[NH:1][C:20](=[O:21])[C:19]([F:26])([F:25])[F:18]
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참가 물질

5

반응물 3

HCID 7915Isopropyl AcetateHCID 9794Ethyl trifluoroacetateHCID 763102-Aminoindane

생성물 1

HCID 10307996N-(2,3-dihydro-1H-inden-2-yl)-2,2,2-trifluoroacetamide수율 83.4%

시약·촉매·용매 1

HCID 8900Heptane용매

반응 조건

온도
2.5 °C

실험 절차

A 1 L, 3-necked, round-bottomed flask, equipped with a mechanical stirrer, digital thermometer, cooling bath, and nitrogen inlet-outlet, was charged with 2-aminoindan, (104 g, 0.781 mole) and isopropyl acetate (200 mL) at 20-25° C. The solution was cooled to 0-5° C. Ethyl trifluoroacetate (133 g, 0.936 mol) was added over 40 minutes while maintaining the internal temperature at 0-10° C. (in a 0-5° C. bath). The thick slurry was stirred at 0-10° C. for 2 hours. The reaction mixture is warmed to 20-25° C. over 30 minutes and heptane (60 mL) was added. The slurry was stirred for 30 minutes and the solids were collected by filtration over a polypropylene filter paper in a Büchner funnel with suction. The filter cake was washed with 0.003% (w/v) Stadis-450 (4.5 mg Lot # 200 Dolder)/heptane (3×50 mL) or until the filtrate was colorless. The solids were dried at 60-65° C. under vacuum (10-30 torr) with nitrogen bleeding to obtain 149.2 g (83.4% yield) of N-(2,3-dihydro-1H-inden-2-yl)-2,2,2-trifluoroacetamide as a beige white solid.

후처리

  1. customA 1 L, 3-necked, round-bottomed flask, equipped with a mechanical stirrer
  2. temperaturedigital thermometer, cooling bath, and nitrogen inlet-outlet
  3. temperaturewhile maintaining the internal temperature at 0-10° C. (in a 0-5° C. bath)
  4. temperatureThe reaction mixture is warmed to 20-25° C. over 30 minutes
  5. stirringThe slurry was stirred for 30 minutes
  6. filtrationthe solids were collected by filtration over a polypropylene
  7. filtrationfilter paper in a Büchner funnel with suction
  8. washThe filter cake was washed with 0.003% (w/v) Stadis-450 (4.5 mg Lot # 200 Dolder)/heptane (3×50 mL)
  9. customThe solids were dried at 60-65° C. under vacuum (10-30 torr) with nitrogen bleeding

출처 및 근거

ORD 기록
ord-9280b1117be14774bd18af5475852d93
출처 데이터셋
uspto-grants-2005_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06933410B2

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