2-Chlorobenzaldehyde → HCID 9824364, compound

HRID 1872595Notes

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].[NH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32]CO.N1CCCCC1>>[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:27]2[CH2:28][CH2:29][CH2:30][CH2:31][CH2:32]2)=[O:22])=[CH:7][C:2]=1[Cl:1]

Participants

Reactant 5

HCID 69962-Chlorobenzaldehyde

HCID 8082Piperidine

HCID 199606-Amino-1-hexanol

HCID 707302,4-Dichlorobenzenethiol

HCID 805982-Bromobenzenethiol

Product 1

HCID 9824364HCID 9824364, 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 piperidine. 1H NMR (DMSO-d6, 300 MHz) δ 8.08 (d, J=1.7 Hz, 1H), 7.80 (dd, J=8.1, 1.4 Hz, 1H), 7.63 (dd, J=8.1, 1.7 Hz, 1H), 7.44 (ap dd, J=7.6, 1.5 Hz, 1H), 7.39 (ap d, J=4.8 Hz, 2H), 7.34 (dt, J=7.5, 1.6, 1H), 7.24 (dd, J=7.5, 1.7, 1H), 7.05 (d, J=8.1 Hz, 1H), 3.65 (br m, 2H), 3.53 (br m, 2H), 1.62 (br m, 2H), 1.50 (br m, 4H). HRMS calculated for C20H19N1O1S1Br1Cl1 : 436.0130. Observed: 436.0122.

Sources & evidence

ORD record: ord-6014c56fb84e40bb8197a45f36e1dfbf
Source dataset: uspto-grants-2000_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06110922

Reaction notes

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