Ethanethiol → HCID 10791154, compound

HRID 609812Notes

Reaction equation

HRID 609812 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([C:10]2[S:14][C:13]3[CH:15]=[C:16]([O:19]C)[CH:17]=[CH:18][C:12]=3[C:11]=2[C:21]([C:23]2[CH:28]=[CH:27][C:26]([O:29][CH2:30][CH2:31][N:32]3[CH2:37][CH2:36][CH2:35][CH2:34][CH2:33]3)=[CH:25][CH:24]=2)=[O:22])[CH:5]=[CH:6][C:7]=1[O:8]C.C(S)C.[Cl-].[Al+3].[Cl-].[Cl-]>C(Cl)Cl>[CH3:1][C:2]1[CH:3]=[C:4]([C:10]2[S:14][C:13]3[CH:15]=[C:16]([OH:19])[CH:17]=[CH:18][C:12]=3[C:11]=2[C:21]([C:23]2[CH:28]=[CH:27][C:26]([O:29][CH2:30][CH2:31][N:32]3[CH2:37][CH2:36][CH2:35][CH2:34][CH2:33]3)=[CH:25][CH:24]=2)=[O:22])[CH:5]=[CH:6][C:7]=1[OH:8]

Participants

5

Reactant 3

HCID 6343EthanethiolHCID 6451240Aluminum(III) ChlorideHCID 10839573[2-(3-Methyl-4-methoxyphenyl)-6-methoxybenzo[b]thien-3-yl][4-[2-(1-piperidinyl)ethoxy]phenyl]methanone

Product 1

HCID 10791154HCID 10791154, compoundYield 64%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

By the method described in Example 2, the product of Example 6 (640 mg, 1.24 mmol), ethanethiol (0.45 mL, 6.18 mmol), and aluminum chloride (1.16 g, 8.70 mmol) were stirred in anhydrous CH2Cl2 (20 mL). After chromatography (silica gel, 5-10% methznol in CH2Cl2), the remnant crystallized from MeOH/CH2Cl2 to give 386 mg (64%) of the title product as a yellow solid: 1H NMR (DMSO-d6) d 1.34 (m, 2H), 1.44 (m, 4H), 2.37 (m, 4H), 2.60 (t, J=5.7 Hz, 2H), 4.05 (t, J=5.7 Hz, 2H), 6.64 (d, J=8.3 Hz, 1H), 6.82 (dd, J=2.1 Hz, 8.8 Hz, 1H), 6.89 (d, J=8.8 Hz, 2H), 6.96 (dd, J=2.1 Hz, 8.3 Hz, 1H), 7.05 (d, J=1.8 Hz, 1H), 7.22 (d, J=8.8 Hz, 1H), 7.30 (d, J=1.8 Hz, 1H), 7.61 (d, J=8.8 Hz, 2H), 9.62 (br s, 1H), 9.75 (br s, 1 H); 13C NMR (DMSO-d6) d 15.7, 23.8, 25.4, 54.2, 57.0, 65.9, 107.0, 114.4, 114.8, 115.1, 123.2, 123.6, 124.3, 126.9, 129.5, 129.7, 130.6, 131.6 , 132.3, 139.1, 140.5, 155.3, 155.9, 162.7, 192.6; MS (FD) m/e 487 (M+); Anal. calc'd. for C29H29NO4S: C, 71.43; H, 6.00; N, 2.87. Found: C, 71.33; H, 6.05; N, 2.92.

Workup

  1. customAfter chromatography (silica gel, 5-10% methznol in CH2Cl2), the remnant crystallized from MeOH/CH2Cl2

Sources & evidence

ORD record
ord-2eb012fe79494b1da31841800b27bf78
Source dataset
uspto-grants-1999_12
Patent number
US05998442

Reaction notes

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