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

HRID 507519

반응식

HRID 507519 반응식
[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

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 241Benzene용매HCID 3283Diethyl Ether용매

실험 절차

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, 6H), 5.93 (s, 2H), 7.19 (dd, J=8, 2 Hz, 1H), 7.37 (d, J=5 Hz, 1H), 7.55 (d, J=5 Hz, 1H), 7.66 (d, J=2 Hz, 1H), 7.94 (d, J=9 Hz, 1H).

후처리

  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

출처 및 근거

ORD 기록
ord-8342a0c1c88440498e843b86ded8c66b
출처 데이터셋
uspto-grants-2010_08
특허 번호
US07786132B2

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