Ethanethiol → [2-(1-Naphthyl)-6-hydroxybenzothien-3-yl][4-[2-(1-piperdinyl)ethoxy]phenyl]methanone

HRID 2192

반응식

HRID 2192 반응식
[C:1]1([C:11]2[S:12][C:13]3[CH:36]=[C:35]([O:37]C)[CH:34]=[CH:33][C:14]=3[C:15]=2[C:16]([C:18]2[CH:23]=[CH:22][C:21]([O:24][CH2:25][CH2:26][N:27]3[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28]3)=[CH:20][CH:19]=2)=[O:17])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.C(S)C.[Cl-].[Al+3].[Cl-].[Cl-]>C(Cl)Cl>[C:1]1([C:11]2[S:12][C:13]3[CH:36]=[C:35]([OH:37])[CH:34]=[CH:33][C:14]=3[C:15]=2[C:16]([C:18]2[CH:19]=[CH:20][C:21]([O:24][CH2:25][CH2:26][N:27]3[CH2:28][CH2:29][CH2:30][CH2:31][CH2:32]3)=[CH:22][CH:23]=2)=[O:17])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1

참가 물질

5

반응물 3

HCID 6343EthanethiolHCID 6451240Aluminum(III) ChlorideHCID 10720792[2-(1-Naphthyl)-6-methoxybenzothien-3-yl][4-[2-(1-piperdinyl)ethoxy]phenyl]methanone

생성물 1

HCID 9806256[2-(1-Naphthyl)-6-hydroxybenzothien-3-yl][4-[2-(1-piperdinyl)ethoxy]phenyl]methanone수율 53.4%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

A solution of the product of Example 1 (1.00 g, 1.92 mmol), ethanethiol (0.45 mL, 6.18 mmol), and aluminum chloride (1.54 g, 11.55 mmol) in anhydrous methylene chloride (40 mL) was stirred for 3.5 hours. The mixture was quenched with saturated potassium sodium tartrate (also known as Rochelle's salt) and extracted with ethyl acetate. The organic layer was washed with saturated sodium potassium tartrate and brine, dried (sodium sulfate), and concentrated. The residue was purified by chromatography (silica gel, 0-10% methanol in methylene chloride) to give 520 mg (53%) of the title product as a dark yellow/green foam: 1H NMR (300 MHz, CDCl3) δ1.46 (m, 2H), 1.65 (m, 4H), 2.54 (m, 4H), 2.73 (t, J=5.4 Hz, 2H), 3.96 (t, J=5.4 Hz, 2H), 6.37 (d, J=8.7 Hz, 2H), 6.88 (dd, J=1.9 Hz, 8.8 Hz, 1H), 7.23-7.29 (m, 2H), 7.37-7.51 (m, 5H), 7.62-7.70 (m, 3H), 8.02-8.05 (m, 1H), 8.28 (br s, 1H); 13C NMR (75 MHz, CDCl3) δ23.3, 24.7, 54.4, 57.0, 64.5, 106.9, 113.0, 115.2, 124.2, 124.3, 125.2, 125.5, 126.1, 127.6, 128.7, 128.7, 130.3, 130.5, 131.2, 131.6, 131.8, 132.8, 133.4, 140.7, 141.1, 154.6, 161.6, 192.1; MS (FD) m/e 508 (MH+); Anal. calc'd. for C32H29NO3S: C, 75.71; H, 5.76; N, 2.76. Found: C, 75.43; H, 6.02; N, 3.03.

후처리

  1. customThe mixture was quenched with saturated potassium sodium tartrate (
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with saturated sodium potassium tartrate and brine
  4. dry with materialdried (sodium sulfate)
  5. concentrationconcentrated
  6. customThe residue was purified by chromatography (silica gel, 0-10% methanol in methylene chloride)

출처 및 근거

ORD 기록
ord-acaaec7f0b624f78bd5144946ae675b0
출처 데이터셋
uspto-grants-1998_03
특허 번호
US05728724

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