2-Chlorobenzaldehyde → HCID 9826426, compound

HRID 1815467Notes

Reaction equation

HRID 1815467 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.[C:45]([NH:48][CH:49]1[CH2:53][CH2:52][NH:51][CH2:50]1)(=[O:47])[CH3:46]>>[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:51]2[CH2:52][CH2:53][CH:49]([NH:48][C:45](=[O:47])[CH3:46])[CH2:50]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 5227153-AcetamidopyrrolidineHCID 5938663-Chloro-4-fluorobenzaldehyde

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-benzaldehyde, 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, 1.7Hz, 1H), 7.80 (d, J=7.8Hz, 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, 1.81 (ap d, J=1.4 Hz, 1H). HRMS calculated for C21H20N2O2S1Br1Cl1: 479.0196. Observed: 479.0183.

Sources & evidence

ORD record
ord-76bb21b29f854c8dba0c84110b3e8900
Source dataset
uspto-grants-2005_04
Patent number
US06878700B1

Reaction notes

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