Malononitrile → [1-(3-Methoxyphenyl)ethylidene]propanedinitrile

HRID 573545노트

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HRID 573545 반응식
C[Si](C)(C)N[Si](C)(C)C.[C:10](#[N:14])[CH2:11][C:12]#[N:13].[CH3:15][C:16]([C:18]1[CH:23]=[CH:22][CH:21]=[C:20]([O:24][CH3:25])[CH:19]=1)=O>C(O)(=O)C>[CH3:25][O:24][C:20]1[CH:19]=[C:18]([C:16](=[C:11]([C:10]#[N:14])[C:12]#[N:13])[CH3:15])[CH:23]=[CH:22][CH:21]=1

참가 물질

5

반응물 3

HCID 8010MalononitrileHCID 114603-MethoxyacetophenoneHCID 13838Hexamethyldisilazane

생성물 1

HCID 247355[1-(3-Methoxyphenyl)ethylidene]propanedinitrile수율 100.9%

시약·촉매·용매 1

HCID 176Acetic Acid용매2회

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온도
70 °C

실험 절차

To a stirred solution of acetic acid (60 mL) was added hexamethyldisilazane (26.2 mL, 125 mmol) dropwise over 30 min with temperature kept below 40° C. throughout addition. This resulting solution was subsequently added to a stirred solution of malononitrile (13.50 g, 204 mmol) and 3-methoxyacetophenone (13.71 mL, 100 mmol) in acetic acid (30 mL). The final reaction mixture heated to 70° C. under nitrogen for 16 h. The reaction mixture was cooled to RT, partitioned between toluene and water (150 mL each). The aqueous layer was separated and re-extracted with toluene (2×60 mL). The combined organic layer was dried over Na2SO4 and solvent removed in vacuo, to afford the title compound (20 g). LCMS (A) m/z: 199 [M+1]+, Rt 1.20 min (acidic).

후처리

  1. additionkept below 40° C. throughout addition
  2. customThe final reaction mixture
  3. temperatureThe reaction mixture was cooled to RT
  4. custompartitioned between toluene and water (150 mL each)
  5. customThe aqueous layer was separated
  6. extractionre-extracted with toluene (2×60 mL)
  7. dry with materialThe combined organic layer was dried over Na2SO4 and solvent
  8. customremoved in vacuo

출처 및 근거

ORD 기록
ord-57683380c43049ebb8e76570d90c2b9a
출처 데이터셋
uspto-grants-2015_05
특허 번호
US09029545B2

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