Ethanethiol → [2-(2-Methyl-4-hydroxyphenyl)-6-hydroxybenzo[b]thien-3-yl][4-[2-(1-piperidinyl)ethoxy]phenyl]methanone

HRID 609820Notes

Reaction equation

HRID 609820 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([O:8]C)[CH:5]=[CH:4][C:3]=1[C:10]1[S:14][C:13]2[CH:15]=[C:16]([O:19]C)[CH:17]=[CH:18][C:12]=2[C:11]=1[C:21]([C:23]1[CH:28]=[CH:27][C:26]([O:29][CH2:30][CH2:31][N:32]2[CH2:37][CH2:36][CH2:35][CH2:34][CH2:33]2)=[CH:25][CH:24]=1)=[O:22].C(S)C.[Cl-].[Al+3].[Cl-].[Cl-]>C(Cl)Cl>[CH3:1][C:2]1[CH:7]=[C:6]([OH:8])[CH:5]=[CH:4][C:3]=1[C:10]1[S:14][C:13]2[CH:15]=[C:16]([OH:19])[CH:17]=[CH:18][C:12]=2[C:11]=1[C:21]([C:23]1[CH:28]=[CH:27][C:26]([O:29][CH2:30][CH2:31][N:32]2[CH2:37][CH2:36][CH2:35][CH2:34][CH2:33]2)=[CH:25][CH:24]=1)=[O:22]

Participants

5

Reactant 3

HCID 6343EthanethiolHCID 6451240Aluminum(III) ChlorideHCID 10720639[2-(2-Methyl-4-methoxyphenyl)-6-methoxybenzo[b]thien-3-yl][4-[2-(1-piperidinyl)ethoxy]phenyl]methanone

Product 1

HCID 10528985[2-(2-Methyl-4-hydroxyphenyl)-6-hydroxybenzo[b]thien-3-yl][4-[2-(1-piperidinyl)ethoxy]phenyl]methanoneYield 27.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

By the method described in Example 2, the product of Example 15 (1.0 g, 1.94 mmol), ethanethiol (0.71 mL, 9.75 mmol), and aluminum chloride (1.81 g, 13.57 mmol) were stirred in anhydrous CH2Cl2 (40 mL). Purification by chromatography (silica gel, 5-10% MeOH in CH2Cl2), provided 260 mg (27%) of the title product as a dark yellow foam: 1H NMR d 1.47 (m, 2H), 1.61 (m, 4H), 2.13 (s, 3H), 2.55 (m, 4H), 2.77 (t, J=5.5 Hz, 2H), 4.09 (t, J=5.5 Hz, 2H), 4.87 (s, 2H), 6.45 (m, 2H), 6.77 (d, J=8.7 Hz, 2H), 6.87 (dd, J=2.2, 8.8 Hz, 1H), 7.01 (d, J=9.1 Hz, 1H), 7.23 (d, J=2.2 Hz, 1H), 7.51 (d, J=8.8 Hz, 1H), 7.60 (d, J=8.7 Hz, 2H); MS (FD) m/e 488 (MH+); HRMS (FAB) m/e calc'd. for C29H30N1O4S1 : 488.1896, found: 488.1911.

Workup

  1. customPurification by chromatography (silica gel, 5-10% MeOH in CH2Cl2)

Sources & evidence

ORD record
ord-27ae9b731c1c4c8996ab47faf5fdac6e
Source dataset
uspto-grants-1999_12
Patent number
US05998442

Reaction notes

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