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

HRID 2194

Reaction equation

HRID 2194 reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[C:11]1[S:12][C:13]2[CH:36]=[C:35]([O:37]C)[CH:34]=[CH:33][C:14]=2[C:15]=1[C:16]([C:18]1[CH:23]=[CH:22][C:21]([O:24][CH2:25][CH2:26][N:27]2[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28]2)=[CH:20][CH:19]=1)=[O:17].C(S)C.[Cl-].[Al+3].[Cl-].[Cl-].CO>C(Cl)Cl>[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[C:11]1[S:12][C:13]2[CH:36]=[C:35]([OH:37])[CH:34]=[CH:33][C:14]=2[C:15]=1[C:16]([C:18]1[CH:19]=[CH:20][C:21]([O:24][CH2:25][CH2:26][N:27]2[CH2:28][CH2:29][CH2:30][CH2:31][CH2:32]2)=[CH:22][CH:23]=1)=[O:17]

Participants

6

Reactant 4

HCID 887MethanolHCID 6343EthanethiolHCID 6451240Aluminum(III) ChlorideHCID 10673572[2-(2-Naphthyl)-6-methoxybenzothien-3-yl][4-[2-(1-piperdinyl)ethoxy]phenyl]methanone

Product 1

HCID 10744215[2-(2-Naphthyl)-6-hydroxybenzothien-3-yl][4-[2-(1-piperdinyl)ethoxy]phenyl]methanoneYield 98.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

By the method described in Example 2, the product of Example 3 (1.35 g, 2.59 mmol), ethanethiol (0.56 mL, 7.69 mmol), and aluminum chloride (2.07 g, 15.52 mmol) were reacted in anhydrous methylene chloride (50 mL) to give, after chromatography (silica gel, 5% methanol in methylene chloride) 1.29 g (98%) of the title product as a yellow foam; 1H NMR (300 MHz, CDCl3) δ1.46 (m, 2H), 1.66 (M, 4H), 2.58 (m, 4H), 2.77 (t, J=5.5 Hz, 2H), 4.04 (t, J=5.5 Hz, 2H), 6.54 (d, J=8.9 Hz, 2H), 6.75 (dd, J=2.2 Hz, 8.8 Hz, 1H), 7.20 (d, J=2.2 Hz, 1H), 7.39-7.46 (m, 4H) 7.64 (d, J=8.6 Hz, 1H), 7.69-7.76 (m, 4H), 7.86 (d, J=1.5 Hz, 1H); 13C NMR (75 MHz, DMSO--d6) δ23.3, 24.9, 53.7, 56.4, 65.3, 106.7, 114.0, 115.0, 123.2, 125.4, 126.3, 126.3, 126.9, 127.0, 127.5, 127.9, 129.1, 130.0, 131.1, 131.2, 131.7, 131.8, 132.1, 138.9, 139.4, 155.4, 162.4, 191.9; MS (FD) m/e 508 (MH+), 507 (M+); Anal. calc'd. for C32H29NO3S: C, 75.71; H, 5.76; N, 2.76. Found: C, 75.86; H, 5.82; N, 2.75.

Workup

  1. customto give

Sources & evidence

ORD record
ord-c366215603d74e8f80c204c070b5fd26
Source dataset
uspto-grants-1998_03
Patent number
US05728724

Linked notes

Loading…