2-Chlorobenzaldehyde → (2-Bromophenyl)[2-chloro-4-(E-((4-acetylhomopiperazin-1-yl)carbonyl) ethenyl)phenyl]sulfide

HRID 984452Notes

Reaction equation

HRID 984452 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6](Cl)[CH:5]=[CH:4][C:3]=1[SH:9].[Br:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1S.ClC1C=CC=[CH:23][C:20]=1[CH:21]=[O:22].ClC1C=C(C=CC=1F)C=O.NCCCCCCO.[C:45]([N:48]1[CH2:54][CH2:53][CH2:52][NH:51][CH2:50][CH2:49]1)(=[O:47])[CH3:46]>>[Br:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[S:9][C:3]1[CH:4]=[CH:5][C:6](/[CH:23]=[CH:20]/[C:21]([N:51]2[CH2:52][CH2:53][CH2:54][N:48]([C:45](=[O:47])[CH3:46])[CH2:49][CH2:50]2)=[O:22])=[CH:7][C:2]=1[Cl:1]

Participants

7

Reactant 6

HCID 69962-ChlorobenzaldehydeHCID 199606-Amino-1-hexanolHCID 707302,4-DichlorobenzenethiolHCID 805982-BromobenzenethiolHCID 5938663-Chloro-4-fluorobenzaldehydeHCID 4186202N-Acetylhomopiperazine

Product 1

HCID 9805756(2-Bromophenyl)[2-chloro-4-(E-((4-acetylhomopiperazin-1-yl)carbonyl) ethenyl)phenyl]sulfide

Procedure

The title compound was prepared by the procedures described in Example 1 substituting 2,4-dichlorothiophenol with 2-bromothiophenol, 2-chlorobenzaldehyde with 3-chloro-4-fluoro-benzaldehyde, and 6-amino-1-hexanol with 4-acetylhomopiperazine. 1H NMR (DMSO-d6, 300 MHz) δ 8.10 (m, 1H), 7.81 (d, J=7.7 Hz, 1H), 7.64 (m, 1H), 7.24-7.51 (m, 5H), 7.05 (m, 1H), 3.39-3.77 (m, 8H), 1.97 (m, 3H), 1.68 (m, 2H). HRMS calculated for C22H22N2O2S1Br1Cl1: 493.0352. Observed: 493.0352.

Sources & evidence

ORD record
ord-6cfc7eeaddbd4060b1b42150ac8e0929
Source dataset
uspto-grants-2005_03
Patent number
US06867203B2

Reaction notes

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