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Dimethylcarbamoyl Chloride → 3-Cyclopropylpyridine-2-carbonitrile

HRID 2238669
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HRID 2238669 반응식
[CH:1]1([C:4]2[CH:5]=[N+:6]([O-])[CH:7]=[CH:8][CH:9]=2)[CH2:3][CH2:2]1.C[Si]([C:15]#[N:16])(C)C.CN(C)C(Cl)=O.C(=O)([O-])[O-].[K+].[K+]>C(Cl)(Cl)Cl>[CH:1]1([C:4]2[C:5]([C:15]#[N:16])=[N:6][CH:7]=[CH:8][CH:9]=2)[CH2:3][CH2:2]1
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참가 물질

6

반응물 4

HCID 6598Dimethylcarbamoyl ChlorideHCID 11430Potassium CarbonateHCID 82115Trimethylsilyl cyanideHCID 45079753Pyridine, 3-cyclopropyl-, 1-oxide

생성물 1

HCID 534257253-Cyclopropylpyridine-2-carbonitrile

시약·촉매·용매 1

HCID 6212Chloroform용매2회

실험 절차

1.47 g of 3-cyclopropylpyridine-1-oxide [121-1] was dissolved in 15 mL of chloroform, and 1.89 mL of trimethylsilyl cyanide was added thereto. Subsequently, a solution prepared by dissolving 1.3 mL of dimethylcarbamoyl chloride in 5 mL of chloroform was added dropwise over 30 minutes, and was stirred overnight at room temperature. Thereto, 10 mL of 10% aqueous solution of potassium carbonate was added, and the mixture was extracted with chloroform. The organic layer was washed with saturated brine, and dried over anhydrous sodium sulfate. The insolubles were filtered and the filtrate was concentrated under reduced pressure, to obtain a residue. The residue was purified by silica gel column chromatography, and 680 mg of 3-cyclopropylpyridine-2-carbonitrile [121-2] was obtained as a white solid.

후처리

  1. customSubsequently, a solution prepared
  2. additionwas added dropwise over 30 minutes
  3. extractionthe mixture was extracted with chloroform
  4. washThe organic layer was washed with saturated brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationThe insolubles were filtered
  7. concentrationthe filtrate was concentrated under reduced pressure
  8. customto obtain a residue
  9. customThe residue was purified by silica gel column chromatography

출처 및 근거

ORD 기록
ord-510a60675709422a82d5de9ac39d5b04
출처 데이터셋
uspto-grants-2010_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07718801B2

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