2-Chlorobenzaldehyde → HCID 178520490, compound

HRID 1815471Notes

Reaction equation

HRID 1815471 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.[NH:45]1[CH2:50][CH2:49][S:48][CH2:47][CH2:46]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:23]=[CH:20]/[C:21]([SH:48]2[CH2:49][CH2:50][NH:45][CH2:46][CH2:47]2)=[O:22])=[CH:7][C:2]=1[Cl:1]

Participants

7

Reactant 6

HCID 69962-ChlorobenzaldehydeHCID 199606-Amino-1-hexanolHCID 67164ThiomorpholineHCID 707302,4-DichlorobenzenethiolHCID 805982-BromobenzenethiolHCID 5938663-Chloro-4-fluorobenzaldehyde

Product 1

HCID 178520490HCID 178520490, 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 thiomorpholine. 1H NMR (DMSO-d6, 300 MHz) δ 8.10 (d, J=1.5 Hz, 1H), 7.80 (d, J=8.5 Hz, 1H), 7.64 (dd, J=8.1, 1.5 Hz, 1H), 7.31-7.48 (m, 4H), 7.36 (m, 1H), 7.26 (dd, J=8.1, 1.8 Hz, 1H), 7.05 (d J=8.1 Hz, 1H), 3.96 (m, 2H), 3.82 (m, 2H), 2.62 (m, 4H). HRMS calculated for C19H17N1O1S2Br1Cl1: 455.9681. Observed: 455.9676.

Sources & evidence

ORD record
ord-7651976e77384669be87b60183ccaf39
Source dataset
uspto-grants-2005_04
Patent number
US06878700B1

Reaction notes

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