2-Chlorobenzaldehyde → HCID 11712945, compound

HRID 1815488Notes

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=C[CH:24]=[CH:23][C:20]=1[CH:21]=[O:22].ClC1C=C(C=CC=1Cl)C=O.NCCCCCCO.[NH2:45][CH2:46][CH2:47][CH2:48][N:49]1C[CH2:52][CH2:51][C:50]1=[O:54]>>[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:52]=[CH:51]/[C:50]([NH:49][CH2:48][CH2:47][CH2:46][N:45]2[CH2:24][CH2:23][CH2:20][C:21]2=[O:22])=[O:54])=[CH:7][C:2]=1[Cl:1]

Participants

Reactant 6

HCID 69962-Chlorobenzaldehyde

HCID 199606-Amino-1-hexanol

HCID 227103,4-Dichlorobenzaldehyde

HCID 707302,4-Dichlorobenzenethiol

HCID 805982-Bromobenzenethiol

HCID 821111-(3-Aminopropyl)-2-pyrrolidinone

Product 1

HCID 11712945HCID 11712945, compound

Procedure

The title compound was prepared by the procedures described in Example 1 substituting 2,4 dichlorothiophenol with 2-bromothiophenol, 2-chlorobenzaldehyde with 3,4 dichlorobenzaldehyde, and 6-amino-1-hexanol with 1-(3-aminopropyl)-2-pyrrolidinone. 1H-NMR (DMSO-d6, 300 MHz) δ 8.12 (t, J=5.9 Hz, 1H), 7.81 (m, 2H), 7.52 (dd, J=8.1, 2.0 Hz, 1H), 7.44 (dt, J=7.5, 1.4, 1H), 7.34 (dt, J=7.5, 2.0, 1H), 7.39 (d, J=15.8 Hz, 1H), 7.28 (dd, J=7.6, 1.9 Hz, 1H), 7.05 (d, J=8.1 Hz, 1H), 6.67 (d, J=15.8 Hz, 1H), 4.02 (d, J=0.7 Hz, 1H), 3.29-3.35 (m, 2H), 3.11-3.25 (m, 4H), 2.21 (t, J=8.1 Hz, 1H), 1.94 (m, 2H), 1.64 (m, 2H), MS(APCI) (M+H)+ at m/z 493, 495, 497,499.

Sources & evidence

ORD record: ord-4260c518181b47c9956fefcc0af9cbd1
Source dataset: uspto-grants-2005_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06878700B1

Reaction notes

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