2-Chlorobenzaldehyde → HCID 9912394, compound

HRID 1815465Notes

Reaction equation

HRID 1815465 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].ClC1C=C(C=CC=1F)C=O.NCCCCCCO.[OH:45][CH2:46][CH:47]1[CH2:52][CH2:51][CH2:50][NH:49][CH2:48]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:49]2[CH2:50][CH2:51][CH2:52][CH:47]([CH2:46][OH:45])[CH2:48]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 107308Piperidin-3-ylmethanolHCID 5938663-Chloro-4-fluorobenzaldehyde

Product 1

HCID 9912394HCID 9912394, 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-benzaldehyde, and 6-amino-1-hexanol with 3-hydroxymethylpiperidine. 1H NMR (DMSO-d6, 300 MHz) δ 8.07 (d, J=17.7 Hz, 1H), 7.80 (d, J=7.7 Hz, 1H), 7.63 (br d, J=7.7 Hz, 1H), 7.44 (d, J=7.0 Hz, 1H), 7.40 (br s, 2H), 7.35 (m, 1H), 7.25 (dd 7.7, 1.5, 1H), 7.06 (dd, J=8.1, 2.9, 1H), 4.57 (m, 1H), 4.45 (m, 1H), 4.16 (br m, 2H), 1.2-1.8 (m, 8H). HRMS calculated for C21H21N1O2S1Br1Cl1: 466.0243. Observed: 466.0247.

Sources & evidence

ORD record
ord-37fc7edb033f4941b7a5b32d7705ad37
Source dataset
uspto-grants-2005_04
Patent number
US06878700B1

Reaction notes

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