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Dimethylformamide → 9-Benzyl-3-formylcarbazole

HRID 659614
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HRID 659614 반응식
CN(C)[CH:3]=[O:4].O=P(Cl)(Cl)Cl.[CH2:11]([N:18]1[C:30]2[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=2[C:24]2[C:19]1=[CH:20][CH:21]=[CH:22][CH:23]=2)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>CCOC(C)=O>[CH2:11]([N:18]1[C:19]2[CH:20]=[CH:21][C:22]([CH:3]=[O:4])=[CH:23][C:24]=2[C:25]2[C:30]1=[CH:29][CH:28]=[CH:27][CH:26]=2)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 3

HCID 6228DimethylformamideHCID 24813Phosphorus oxychlorideHCID 146485N-Benzylcarbazole

생성물 1

HCID 30915349-Benzyl-3-formylcarbazole수율 36.3%

시약·촉매·용매 1

HCID 8857Ethyl Acetate용매

반응 조건

온도
0 °C

실험 절차

A 50-mL 3-necked round-bottomed flask was charged with N,N-dimethylformamide (400 mg, 5.42 mmol, 2.80 equiv, 99%). To this, POCl3 (700 mg, 4.56 mmol, 2.40 equiv, 99%) was added drop wise with stirring at 0° C. and allowed to stir at room temperature for 1 hour. To this mixture was added 9-benzyl-9H-carbazole (500 mg, 1.93 mmol, 1.00 equiv, 99%) in small portions at 45° C. over 5 minutes. Then, the temperature was raised to 95° C. in an oil bath and allowed to stir for 18 hours. The progress was monitored by TLC (EtOAc:PE=1:4). Upon completion, the reaction mixture was cooled down to room temperature and quenched with water (20 mL). The resulting mixture was allowed to stir for an additional 4 hours at room temperature. The solids were collected by filtration and dried to afford 9-benzyl-9H-carbazole-3-carbaldehyde as green solid (200 mg, 36.1%). LCMS: [M+H]+: 286

후처리

  1. stirringto stir at room temperature for 1 hour
  2. temperatureThen, the temperature was raised to 95° C. in an oil bath
  3. stirringto stir for 18 hours
  4. temperatureUpon completion, the reaction mixture was cooled down to room temperature
  5. customquenched with water (20 mL)
  6. stirringto stir for an additional 4 hours at room temperature
  7. filtrationThe solids were collected by filtration
  8. customdried

출처 및 근거

ORD 기록
ord-51d5def88816466c93d27c67a79c1724
출처 데이터셋
uspto-grants-2011_12
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08080566B1

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