N-Methylbutylamine → Methyl 5-{[butyl(methyl)amino]methyl}thiophene-2-carboxylate

HRID 348900

반응식

HRID 348900 반응식
Br[CH2:2][C:3]1[S:7][C:6]([C:8]([O:10][CH3:11])=[O:9])=[CH:5][CH:4]=1.[CH3:12][NH:13][CH2:14][CH2:15][CH2:16][CH3:17]>CC(C)=O>[CH2:14]([N:13]([CH2:2][C:3]1[S:7][C:6]([C:8]([O:10][CH3:11])=[O:9])=[CH:5][CH:4]=1)[CH3:12])[CH2:15][CH2:16][CH3:17]

참가 물질

4

반응물 2

HCID 8068N-MethylbutylamineHCID 11424851Methyl 5-(bromomethyl)thiophene-2-carboxylate

생성물 1

HCID 21086213Methyl 5-{[butyl(methyl)amino]methyl}thiophene-2-carboxylate

시약·촉매·용매 1

HCID 180Acetone용매

실험 절차

To a solution of methyl 5-(bromomethyl)thiophene-2-carboxylate (350 mg, 1.49 mmol) in dry acetone (6.0 mL) is added N-methylbutylamine (533 μL, 4.47 mmol) and the solution stirred at room temperature overnight. The reaction is then concentrated under reduced pressure, redissolved in methylene chloride, washed with saturated sodium bicarbonate, water, and brine. The organic layer is then dried (sodium sulfate), filtered, and concentrated under reduced pressure to yield the title compound in pure form. 1H NMR (300 MHz, CDCl3) δ 7.65 (d, J=3 Hz, 1H), 6.88 (d, J=3 Hz, 1H), 3.86 (s, 3H), 3.69 (s, 2H), 2.41–2.36 (m, 2H), 2.25 (s, 3H), 1.53–1.43 (m, 2H), 1.34–1.25 (m, 2H), 0.91 (t, J=7 Hz, 3H)

후처리

  1. concentrationThe reaction is then concentrated under reduced pressure
  2. dissolutionredissolved in methylene chloride
  3. washwashed with saturated sodium bicarbonate, water, and brine
  4. dry with materialThe organic layer is then dried (sodium sulfate)
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-218df0caef1643e8b4cf8d84d25386ac
출처 데이터셋
uspto-grants-2007_02
특허 번호
US07176242B2

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