2-Chlorobenzaldehyde → HCID 11664188, compound

HRID 1815485Notes

Reaction equation

HRID 1815485 reaction equation
ClC1C=C(Cl)C=CC=1S.[Br:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[SH:17].ClC1C=CC=C[C:20]=1[CH:21]=[O:22].F[C:28]1[CH:35]=[CH:34][C:31]([CH:32]=O)=[CH:30][C:29]=1[C:36]([F:39])([F:38])[F:37].NCCCCCCO.[N:48]1([C:54]([O:56][C:57]([CH3:60])([CH3:59])[CH3:58])=[O:55])[CH2:53][CH2:52][NH:51][CH2:50][CH2:49]1>O>[Br:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[S:17][C:28]1[CH:35]=[CH:34][C:31](/[CH:32]=[CH:20]/[C:21]([N:51]2[CH2:52][CH2:53][N:48]([C:54]([O:56][C:57]([CH3:60])([CH3:59])[CH3:58])=[O:55])[CH2:49][CH2:50]2)=[O:22])=[CH:30][C:29]=1[C:36]([F:39])([F:38])[F:37]

Participants

8

Reactant 6

HCID 69962-ChlorobenzaldehydeHCID 199606-Amino-1-hexanolHCID 707302,4-DichlorobenzenethiolHCID 805982-BromobenzenethiolHCID 143452tert-Butyl piperazine-1-carboxylateHCID 5222694-Fluoro-3-(trifluoromethyl)benzaldehyde

Product 1

HCID 11664188HCID 11664188, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

The title compound was prepared by the procedures described in Example 1 substituting 2,4-dichlorothiophenol with 2-bromothiophenol, 2-chlorobenzaldehyde with 4-fluoro-3-trifluoromethylbenzaldehyde, and 6-amino-1-hexanol with t-butyl 1-piperazinecarboxylate, to give a white solid. 1H NMR (CDCl3, 300 MHz) d 1.48 (s, 9H), 3.49 (br s, 4H), 3.56-3.78 (m, 4H), 6.89 (d, J=15.6 Hz, 1H), 7.10 (d, J=8.4 Hz, 1H), 7.18-7.35 (m, 3H), 7.49 (d, J=8.4 Hz, 1H), 7.65 (d, J=15.6 Hz, 1H), 7.68 (dd, J=2.1, 8.4 Hz, 1H), 7.85 (br s, 1H). MS (APCI−) (M+Cl)− at m/z 605, 607, 609. Anal. Calcd for C25H26N2O3BrF3S. 0.03 H2O: C, 52.50; H, 4.59; N, 4.90. Found: C, 52.54; H, 4.71; N, 4.68.

Workup

  1. customto give a white solid

Sources & evidence

ORD record
ord-2e2db83e82b040ca9630341aa04deefb
Source dataset
uspto-grants-2005_04
Patent number
US06878700B1

Reaction notes

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