Diisopropylamine → 2-Pyridylmalononitrile

HRID 490108

반응식

HRID 490108 반응식
[CH:1]([NH:4]C(C)C)(C)C.[Li]CCCC.C1COCC1.[N:18]1[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=1[CH2:24][C:25]#[N:26].ClC1C=CC=CC=1CSC#N>C1(C)C=CC=CC=1.O>[N:18]1[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=1[CH:24]([C:1]#[N:4])[C:25]#[N:26]

참가 물질

7

반응물 4

HCID 7912DiisopropylamineHCID 75959Pyridine-2-acetonitrileHCID 2867232-Chlorobenzyl ThiocyanateHCID 178420697HCID 178420697, 화합물

생성물 1

HCID 102409162-Pyridylmalononitrile수율 63.4%

시약·촉매·용매 2

HCID 962Water용매HCID 1140Toluene용매2회

반응 조건

온도
0 °C

실험 절차

To diisopropylamine (15.3 mL, 109 mmol) in toluene (500 mL), at 0-5° C., under nitrogen, was added drop wise over ˜½ hour 1.6M″ BuLi/THF (68.5 mL, 109 mmol). The reaction mixture was stirred for a further 15 minutes before the drop wise addition of 2-pyridylacetonitrile (5.55 mL, 49.6 mmol) over 1 hour. 2-Chlorobenzylthiocyanate (20.0 g, 109 mmol), described in the literature by Schlesinger J. Am. Chem. Soc. 1954, 76, 585, was then added in solution in toluene (100 mL) over a period of 1 hour. The reaction mixture was stirred for an additional 2 hours. Water was added and the layers were separated. The organic phase was extracted twice with 200 mL 2N NaOH. The combined aqueous phases were cooled down to 0° C and acidified to ˜pH 1. The precipitate obtained was filtered and dried to give the title compound as a pale tan solid (4.50 g, 63% yield). δH (DMSO-d6) 6.79 (1H, t), 7.09 (1H, d), 7.73 (1H, t), 7.79 (1H, dd), 12.95 (1H, br s).

후처리

  1. customthe layers were separated
  2. extractionThe organic phase was extracted twice with 200 mL 2N NaOH
  3. customThe precipitate obtained
  4. filtrationwas filtered
  5. customdried

출처 및 근거

ORD 기록
ord-67eef88b60804d5e82bbd99ccbcd8b24
출처 데이터셋
uspto-grants-2009_05
특허 번호
US07528138B2

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