2-Chlorobenzaldehyde → HCID 9933605, compound

HRID 1872594Notes

Reaction equation

HRID 1872594 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.Cl[C:19]1C=CC=C[C:20]=1[CH:21]=[O:22].NCCCCCCO.[OH:35][CH:36]1[CH2:41][CH2:40][NH:39][CH2:38][CH2:37]1>>[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:19]=[CH:20]/[C:21]([N:39]2[CH2:40][CH2:41][CH:36]([OH:35])[CH2:37][CH2:38]2)=[O:22])=[CH:7][C:2]=1[Cl:1]

Participants

6

Reactant 5

HCID 69962-ChlorobenzaldehydeHCID 199606-Amino-1-hexanolHCID 707302,4-DichlorobenzenethiolHCID 79341Piperidin-4-olHCID 805982-Bromobenzenethiol

Product 1

HCID 9933605HCID 9933605, compound

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-hydroxypiperidine. 1H NMR (DMSO-d6, 300 MHz) δ 8.08 (d, J=1.7 Hz, 1H), 7.80 (dd, J=8.0, 1.5 Hz, 1H), 7.63 (dd, J=8.3, 1.9 Hz, 1H), 7.44 (ap dd, J=7.5, 1.4 Hz, 2H), 7.40 (ap d, J=3.7 Hz 2H), 7.34 (dt, J=7.6, 1.8 Hz, 1H), 7.25 (dd, J=7.5,1.7 Hz 1H), 7.05 (d, J=8.1 Hz, 1H), 4.76 (br s, 1H), 4.01 (m, 2H), 3.72 (m, 1H), 3.12 (m, 1H), 1.75 (m, 2H), 1.32 (m, 2H). HRMS calculated for C20H19N1O2S1Br1Cl1 : 452.0087. Observed: 452.0076.

Sources & evidence

ORD record
ord-fde4ff41aa6b48bdb67c1d5ba9b0b785
Source dataset
uspto-grants-2000_08
Patent number
US06110922

Reaction notes

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