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

HRID 1872596Notes

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].NCCCCCCO.[C:35]([N:38]1[CH2:44][CH2:43][CH2:42][NH:41][CH2:40][CH2:39]1)(=[O:37])[CH3:36]>>[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:41]2[CH2:42][CH2:43][CH2:44][N:38]([C:35](=[O:37])[CH3:36])[CH2:39][CH2:40]2)=[O:22])=[CH:7][C:2]=1[Cl:1]

Participants

Reactant 5

HCID 69962-Chlorobenzaldehyde

HCID 199606-Amino-1-hexanol

HCID 707302,4-Dichlorobenzenethiol

HCID 805982-Bromobenzenethiol

HCID 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-benzadehyde, 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-842c52242269492eaf35edea5453cb0f
Source dataset: uspto-grants-2000_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06110922

Reaction notes

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