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1,2-Dibromoethane → 1-(6-Chloropyridazin-3-yl)cyclopropane-1-carbonitrile

HRID 1528568
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HRID 1528568 반응식
[OH-].[Na+].[Cl:3][C:4]1[N:9]=[N:8][C:7]([CH2:10][C:11]#[N:12])=[CH:6][CH:5]=1.Br[CH2:14][CH2:15]Br>[Cl-].C([N+](CCCC)(CCCC)CCCC)C1C=CC=CC=1.C(#N)C>[Cl:3][C:4]1[N:9]=[N:8][C:7]([C:10]2([C:11]#[N:12])[CH2:15][CH2:14]2)=[CH:6][CH:5]=1
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참가 물질

6

반응물 3

HCID 78391,2-DibromoethaneHCID 14798Sodium HydroxideHCID 224447672-(6-Chloropyridazin-3-yl)acetonitrile

생성물 1

HCID 866961331-(6-Chloropyridazin-3-yl)cyclopropane-1-carbonitrile

시약·촉매·용매 2

HCID 159952Benzyltributylammonium chloride촉매HCID 6342Acetonitrile
용매

실험 절차

Aqueous NaOH solution (50%, 5 mL) was added to a solution of (6-chloro-pyridazin-3-yl)-acetonitrile (0.21 g), 1,2-dibromoethane (0.14 mL), and benzyltributylammonium chloride (0.43 g) in acetonitrile (5 mL) at room temperature. The resulting mixture was stirred at room temperature for 4 h and was then extracted with ethyl acetate. The combined extracts were washed with brine and dried (MgSO4). The solvent was evaporated and the residue was chromatographed on silica gel (cyclohexane/ethyl acetate 1:1→0:1) to give the title compound as a solid. Yield: 0.14 g (57% of theory); LC (method 1): tR=1.12 min; Mass spectrum (ESI+): m/z=180/182 (Cl) [M+H]+.

후처리

  1. extractionwas then extracted with ethyl acetate
  2. washThe combined extracts were washed with brine
  3. dry with materialdried (MgSO4)
  4. customThe solvent was evaporated
  5. customthe residue was chromatographed on silica gel (cyclohexane/ethyl acetate 1:1→0:1)

출처 및 근거

ORD 기록
ord-5ac3737e11644e538843f74cf2f5d034
출처 데이터셋
uspto-grants-2015_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09090605B2

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