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Dimethylcarbamoyl Chloride → 6-(4-Chloro-phenyl)-5-cyclopropylmethoxy-pyridine-2-carbonitrile

HRID 1528373
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HRID 1528373 반응식
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:13]([O:14][CH2:15][CH:16]3[CH2:18][CH2:17]3)=[CH:12][CH:11]=[CH:10][N+:9]=2[O-])=[CH:4][CH:3]=1.[CH2:20]([N:22](CC)CC)C.CN(C)C(Cl)=O.C[Si](C#N)(C)C>C(#N)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]=[C:10]([C:20]#[N:22])[CH:11]=[CH:12][C:13]=2[O:14][CH2:15][CH:16]2[CH2:18][CH2:17]2)=[CH:4][CH:3]=1
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 4

HCID 6598Dimethylcarbamoyl ChlorideHCID 8471TriethylamineHCID 82115Trimethylsilyl cyanideHCID 666786042-(4-Chloro-phenyl)-3-cyclopropylmethoxy-pyridine 1-oxide

생성물 1

HCID 666786996-(4-Chloro-phenyl)-5-cyclopropylmethoxy-pyridine-2-carbonitrile수율 59.3%

시약·촉매·용매 1

HCID 6342
Acetonitrile
용매

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온도
90 °C

실험 절차

To a solution of 25 g 2-(4-chloro-phenyl)-3-cyclopropylmethoxy-pyridine 1-oxide in 500 mL acetonitrile, 9.23 g triethylamine and 10.73 g dimethylcarbamoylchlorid were added. After 5 minutes at room temperature, 27.88 g trimethylsilylcyanid was added. The reaction mixture was stirred at 90° C. over 15 h. The reaction mixture was partitioned between water and ethyl acetate; then extracted. The organic phase was washed with brine; then dried over MgSO4 and purified by chromatography on silica gel with a gradient of heptane to heptane:ethyl acetate 2:1 to yield 15.30 g (59.26%) of the title compound as light yellow solid, MS 285.1 (M+H)+.

후처리

  1. customThe reaction mixture was partitioned between water and ethyl acetate
  2. extractionthen extracted
  3. washThe organic phase was washed with brine
  4. dry with materialthen dried over MgSO4
  5. custompurified by chromatography on silica gel with a gradient of heptane to heptane:ethyl acetate 2:1

출처 및 근거

ORD 기록
ord-e453291991294a24a66c3827673e2be1
출처 데이터셋
uspto-grants-2015_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09090599B2

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