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Potassium Carbonate → 2,5-Dichloropyridine-4-carbonitrile

HRID 637791
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HRID 637791 반응식
O=P(Cl)(Cl)Cl.[Cl:6][C:7]1[CH:12]=[C:11]([CH:13]=[N:14]O)[C:10]([Cl:16])=[CH:9][N:8]=1.C([O-])([O-])=O.[K+].[K+]>C(#N)C>[Cl:6][C:7]1[CH:12]=[C:11]([C:13]#[N:14])[C:10]([Cl:16])=[CH:9][N:8]=1
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참가 물질

5

반응물 3

HCID 11430Potassium CarbonateHCID 24813Phosphorus oxychlorideHCID 1363872824-Pyridinecarboxaldehyde, 2,5-dichloro-, oxime

생성물 1

HCID 135602102,5-Dichloropyridine-4-carbonitrile수율 77.4%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

To 100 ml of acetonitrile was added 24.5 g of POCl3, followed by 27.1 g of 2,5-dichloro-4-pyridinecarboxaldehyde oxime (prepared as described in Example 4). The reaction mixture was heated at reflux temperature for 1 hour, then cooled and poured onto 300 g of ice. The pH of the mixture was adjusted to about pH 6 with K2CO3 and filtered. The filtrate was extracted with 100 ml of CH2Cl2. The filter cake and the CH2Cl2 solution were combined, diluted with equal volumes of hexane, treated with charcoal, dried, and concentrated. The residue was purified by distillation on a Kugelrohr distillation apparatus (boiling point 80° C. at 0.2 mm pressure) to give 19.0 g (77%) of the desired 2,5-dichloro-4-pyridinecarbonitrile as a white solid, m.p. 58°-60° C.

후처리

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux temperature for 1 hour
  3. temperaturecooled
  4. filtrationfiltered
  5. extractionThe filtrate was extracted with 100 ml of CH2Cl2
  6. additiondiluted with equal volumes of hexane
  7. additiontreated with charcoal
  8. customdried
  9. concentrationconcentrated
  10. distillationThe residue was purified by distillation on a Kugelrohr distillation apparatus (boiling point 80° C. at 0.2 mm pressure)

출처 및 근거

ORD 기록
ord-ce726209030f425f86002d234f826cb2
출처 데이터셋
uspto-grants-1985_12
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US04558134

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