Acetic Acid → (benzo[b]thiophen-5-yl)-2,5-dimethyl-1H-pyrrole

HRID 2267294

反応式

HRID 2267294 の反応式
[S:1]1[CH:5]=[CH:4][C:3]2[CH:6]=[C:7]([NH2:10])[CH:8]=[CH:9][C:2]1=2.[CH3:11][C:12](=O)[CH2:13][CH2:14][C:15](=O)[CH3:16].C(O)(=O)C>C1C=CC=CC=1.C(OCC)C>[S:1]1[CH:5]=[CH:4][C:3]2[CH:6]=[C:7]([N:10]3[C:15]([CH3:16])=[CH:14][CH:13]=[C:12]3[CH3:11])[CH:8]=[CH:9][C:2]1=2

参加物

6

反応物 3

HCID 176Acetic AcidHCID 80352,5-HexanedioneHCID 288032Benzo(b)thiophen-5-amine

生成物 1

HCID 57428820(benzo[b]thiophen-5-yl)-2,5-dimethyl-1H-pyrrole収率 97%

試薬・触媒・溶媒 2

HCID 241Benzene溶媒HCID 3283Diethyl Ether溶媒

実験手順

A stirred solution of benzo[b]thiophen-5-amine (2.48 g, 17.0 mmol), hexane-2,5-dione (1.95 mL, 17.0 mmol) and glacial acetic acid (0.2 mL) in benzene (35 mL) was heated to reflux under a Dean-Stark head. After 14 h the reaction was cooled to r.t., diluted with diethyl ether (40 mL), and successively washed with aqueous 2 N hydrochloric acid (30 mL), brine (30 mL), a saturated aqueous solution of sodium hydrogen carbonate (30 mL) and finally brine (30 mL). The organic layer was separated, dried over magnesium sulfate, filtered and the solvent evaporated in vacuo to yield 1-(benzo[b]thiophen-5-yl)-2,5-dimethyl-1H-pyrrole (3.67 g, 97%) as a light orange crystalline solid. 1H NMR δ (CDCl3, 400 MHz) 2.04 (s, 6 H), 5.93 (s, 2 H), 7.19 (dd, J=8, 2 Hz, 1 H), 7.37 (d, J=5 Hz, 1 H), 7.55 (d, J=5 Hz, 1 H), 7.66 (d, J=2 Hz, 1 H), 7.94 (d, J=9 Hz, 1 H).

後処理

  1. temperatureto reflux under a Dean-Stark head
  2. washsuccessively washed with aqueous 2 N hydrochloric acid (30 mL), brine (30 mL)
  3. customThe organic layer was separated
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. customthe solvent evaporated in vacuo

出典と根拠

ORDレコード
ord-b66ac67e2823491395836063477b0fd0
出典データセット
uspto-grants-2010_12
特許番号
US07858785B2

関連ノート

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