Sodium hydride → HCID 14989636, 화합물

HRID 1199683

반응식

HRID 1199683 반응식
[H-].[Na+].[C:3]([CH2:5][CH:6]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[C:7]([O:9][CH2:10][CH3:11])=[O:8])#[N:4].Cl[C:18]1[CH:23]=[CH:22][C:21]([N+:24]([O-:26])=[O:25])=[CH:20][N:19]=1>CCCCCC.O1CCCC1>[C:3]([CH2:5][C:6]([C:18]1[CH:23]=[CH:22][C:21]([N+:24]([O-:26])=[O:25])=[CH:20][N:19]=1)([C:7]([O:9][CH2:10][CH3:11])=[O:8])[C:12]([O:14][CH2:15][CH3:16])=[O:13])#[N:4]

참가 물질

6

반응물 3

HCID 24758Sodium hydrideHCID 783082-Chloro-5-nitropyridineHCID 272015Diethyl 2-(cyanomethyl)malonate

생성물 1

HCID 14989636HCID 14989636, 화합물

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매3회HCID 8058Hexane용매

실험 절차

Sodium hydride (53% dispersion in oil) (5.17 g, 0.1 mole) was washed by decantation with hexane (2×150 ml), tetrahydrofuran (THF) (150 ml) and was finally suspended in THF (150 ml). Diethyl 2-(cyanomethyl)malonate (26.4 g, 0.11 mole) in THF (20 ml) was added dropwise over 45 minutes keeping the internal temperature at 18° C. to 22° C. (with ice bath cooling). The resulting suspension cleared over 15 minutes when 2-chloro-5-nitropyridine (14.22 g, 0.09 mole) was added to give a deep magenta solution. The resulting solution was refluxed for 3 hours and the solvent was removed on the rotary evaporator. The resulting oil was partitioned between water (200 ml) and chloroform (200 ml), the pH was adjusted to ~7 (concentrated hydrochloric acid), and the chloroform was run off. The aqueous layer was extracted with a further (2×250 ml) chloroform, the extracts were combined, dried over magnesium sulphate and the solvent was removed to give the title compound as an amber oil. Ether (25 ml) was added and the solution was allowed to crystallise to give the title compound (18.48 g). m.p. 66°-68° C.

후처리

  1. customat 18° C. to 22° C.
  2. temperature(with ice bath cooling)
  3. customto give a deep magenta solution
  4. temperatureThe resulting solution was refluxed for 3 hours
  5. customthe solvent was removed on the rotary evaporator
  6. customThe resulting oil was partitioned between water (200 ml) and chloroform (200 ml)
  7. extractionThe aqueous layer was extracted with a further (2×250 ml) chloroform
  8. dry with materialdried over magnesium sulphate
  9. customthe solvent was removed

출처 및 근거

ORD 기록
ord-a44c859b86f64c01b5f5fa9de7ab4953
출처 데이터셋
uspto-grants-1990_02
특허 번호
US04902698

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