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Acetone → HCID 68292872, 화합물

HRID 1504951
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HRID 1504951 반응식
[Si]([C:5]#[N:6])(C)(C)C.[NH2:7][C:8]1[CH:13]=[CH:12][C:11]([CH2:14][CH2:15][CH2:16][C:17]([NH2:19])=[O:18])=[CH:10][CH:9]=1.[CH3:20][C:21]([CH3:23])=O>>[C:5]([C:21]([NH:7][C:8]1[CH:9]=[CH:10][C:11]([CH2:14][CH2:15][CH2:16][C:17]([NH2:19])=[O:18])=[CH:12][CH:13]=1)([CH3:23])[CH3:20])#[N:6]
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참가 물질

4

반응물 3

HCID 180AcetoneHCID 82115Trimethylsilyl cyanideHCID 54549569HCID 54549569, 화합물

생성물 1

HCID 68292872HCID 68292872, 화합물수율 41.3%

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온도
40 °C

실험 절차

TMSCN (0.3 mL, 2.36 mmol) was added to a mixture of the compound 33 (140 mg, 0.79 mmol), acetone (0.35 mL, 1.56 mmol) and 12 (10 mg, 0.08 mmol). The reaction mixture was stirred at 40° C. for 1 h. The reaction was concentrated in vacuo. The residue was diluted with aqNa2SO3, and extracted with ethyl acetate. The combined organic layers were washed with aqNa2SO3 and brine, dried over Na2SO4 and concentrated to dryness to give compound 34 (80 mg) as a light yellow oil. The crude product was used directly for the next step without purification. 1H NMR (400 MHz, CDCl3) δ7.08 (d, 2H, J=8.5 Hz), 6.88 (d, 2H, J=8.5 Hz), 5.29 (br s, 1H), 2.61 (t, 2H, J=7.4 Hz), 2.20 (t, 2H, J=7.4 Hz), 1.87-1.97 (m, 2H), 1.68 (s, 6H).

후처리

  1. concentrationThe reaction was concentrated in vacuo
  2. additionThe residue was diluted with aqNa2SO3
  3. extractionextracted with ethyl acetate
  4. washThe combined organic layers were washed with aqNa2SO3 and brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated to dryness

출처 및 근거

ORD 기록
ord-9e0dda07c3d2414f93d45261fc9b98f0
출처 데이터셋
uspto-grants-2015_12
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09216957B2

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