2-Chlorobenzaldehyde → HCID 178520490, compound

HRID 1792637Notes

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.[NH:35]1[CH2:40][CH2:39][S:38][CH2:37][CH2:36]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:38]2[CH2:39][CH2:40][NH:35][CH2:36][CH2:37]2)=[O:22])=[CH:7][C:2]=1[Cl:1]

Participants

Reactant 5

HCID 69962-Chlorobenzaldehyde

HCID 199606-Amino-1-hexanol

HCID 67164Thiomorpholine

HCID 707302,4-Dichlorobenzenethiol

HCID 805982-Bromobenzenethiol

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-benzadehyde 3-chloro-3-fluoro-benzaldehyde, and 6-amino-1-hexanol with thiomorpholine. 1H NMR (DMSO-d6, 300 MHz) 68.10 (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-f478e6b09ff24762ac80fdae5aefd5cd
Source dataset: uspto-grants-2006_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: USRE039197E1

Reaction notes

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