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Sodium Carbonate → HCID 58305608, 화합물

HRID 2280277
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HRID 2280277 반응식
O=P(Cl)(Cl)Cl.[CH3:6][C:7]1[CH:8]=[C:9]([CH:13]=[CH:14][C:15]=1[N:16]1[CH:20]=[CH:19][CH:18]=[CH:17]1)[C:10]([NH2:12])=O.[C:21]([O-])([O-])=[O:22].[Na+].[Na+]>CN(C=O)C>[CH:21]([C:17]1[N:16]([C:15]2[CH:14]=[CH:13][C:9]([C:10]#[N:12])=[CH:8][C:7]=2[CH3:6])[CH:20]=[CH:19][CH:18]=1)=[O:22]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 3

HCID 10340Sodium CarbonateHCID 24813Phosphorus oxychlorideHCID 58305652HCID 58305652, 화합물

생성물 1

HCID 58305608HCID 58305608, 화합물수율 68%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매2회

실험 절차

POCl3 (65 g, 427 mmol) was added to DMF (34 mL) at 0° C. for 30 min. After addition, the mixture was stirred at room temperature for 1.5 h, and then cooled to 0° C. A solution of 3-methyl-4-(1H-pyrrol-1-yl)benzamide (6A) (42.7 g, 213.5 mmol) in DMF (150 mL) was added at 0° C. and the resultant mixture was stirred at room temperature for 20 min, and then heated to 80° C. for 1 h. The solution was cooled to room temperature and then sat. Na2CO3 was added at 0° C. until pH=8. The mixture was extracted with ethyl acetate three times. The combined organic layers were washed with sat. NaHCO3 and brine, dried over Na2SO4, concentrated and purified by silica gel column chromatography (PE:EA=10:1) to afford 4-(2-formyl-1H-pyrrol-1-yl)-3-methylbenzonitrile as a yellow solid (30.5 g, yield 68%).

후처리

  1. additionAfter addition
  2. temperaturecooled to 0° C
  3. temperatureheated to 80° C. for 1 h
  4. temperatureThe solution was cooled to room temperature
  5. extractionThe mixture was extracted with ethyl acetate three times
  6. washThe combined organic layers were washed with sat. NaHCO3 and brine
  7. dry with materialdried over Na2SO4
  8. concentrationconcentrated
  9. custompurified by silica gel column chromatography (PE:EA=10:1)

출처 및 근거

ORD 기록
ord-b7bc37e65c7f4c298af3c319f81f1aae
출처 데이터셋
uspto-grants-2015_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09138427B2

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