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

HRID 14108

反応式

HRID 14108 の反応式
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]

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 180Acetone溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-9aaf626347dc44ce96bbc4c487c5589d
出典データセット
uspto-grants-2010_06
特許番号
US07727997B2

関連ノート

読み込み中…