2-Chlorobenzaldehyde → HCID 9826426, compound

HRID 1872593Notes

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.[C:35]([NH:38][CH:39]1[CH2:43][CH2:42][NH:41][CH2:40]1)(=[O:37])[CH3:36]>>[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:41]2[CH2:42][CH2:43][CH:39]([NH:38][C:35](=[O:37])[CH3:36])[CH2:40]2)=[O:22])=[CH:7][C:2]=1[Cl:1]

Participants

Reactant 5

HCID 69962-Chlorobenzaldehyde

HCID 199606-Amino-1-hexanol

HCID 707302,4-Dichlorobenzenethiol

HCID 805982-Bromobenzenethiol

HCID 5227153-Acetamidopyrrolidine

Product 1

HCID 9826426HCID 9826426, 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 3-acetamidopyrrolidine. 1H NMR (DMSO-d6, 300 MHz) δ 8.14 (m, 1H), 8.07 (dd, J=9.8, 1.7 Hz, 1H), 7.80 (d, J=7.8 Hz, 1H), 7.64 (dd, J=8.1, 1.7 Hz, 1H), 7.25-7.47 (m, 4H), 7.10 (t, J=7.8 Hz, 1H), 7.03 (dd, J=8.1, 1.7 Hz, 1H), 3.45-4.34 (m, 6H), 2.02 (m, 2H), 1.81 (ap d, J=1.4 Hz, 1H). HRMS calculated for C21H20N2O2S1Br1Cl1 : 479.0196. Observed: 479.0183.

Sources & evidence

ORD record: ord-e99b208461df43ccb5b03574486c1d88
Source dataset: uspto-grants-2000_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06110922

Reaction notes

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