3-(3,5,5,8,8-Pentamethyl-5,6,7,8-tetrahydronaphthalen-2-yl)-4-methoxy-benzaldehyde → 5-[4-Methoxy-3-(3,5,5,8,8-pentamethyl-5,6,7,8-tetrahydro-naphthalen-2-yl)-benzylidene]-3-(2-pyridin-2-yl-ethyl)-thiazolidine-2,4-dione
Reaction equation
[CH3:1][O:2][C:3]1[CH:10]=[CH:9][C:6]([CH:7]=O)=[CH:5][C:4]=1[C:11]1[C:20]([CH3:21])=[CH:19][C:18]2[C:17]([CH3:23])([CH3:22])[CH2:16][CH2:15][C:14]([CH3:25])([CH3:24])[C:13]=2[CH:12]=1.[N:26]1[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=1[CH2:32][CH2:33][N:34]1[C:38](=[O:39])[CH2:37][S:36][C:35]1=[O:40]>>[CH3:1][O:2][C:3]1[CH:10]=[CH:9][C:6]([CH:7]=[C:37]2[S:36][C:35](=[O:40])[N:34]([CH2:33][CH2:32][C:27]3[CH:28]=[CH:29][CH:30]=[CH:31][N:26]=3)[C:38]2=[O:39])=[CH:5][C:4]=1[C:11]1[C:20]([CH3:21])=[CH:19][C:18]2[C:17]([CH3:23])([CH3:22])[CH2:16][CH2:15][C:14]([CH3:25])([CH3:24])[C:13]=2[CH:12]=1Participants
3
Reactant 2
Product 1
Procedure
5-[4-Methoxy-3-(3,5,5,8,8-pentamethyl-5,6,7,8-tetrahydro-naphthalen-2-yl)-benzylidene]-3-(2-pyridin-2-yl-ethyl)-thiazolidine-2,4-dione was prepared in a similar manner as described in Example 1 using 4-methoxy-3-(3,5,5,8,8-pentamethyl-5,6,7,8-tetrahydro-naphthalen-2-yl) benzaldehyde and 3-(2-pyridin-2-yl-ethyl)-thiazolidine-2,4-dione, mp 170–171° C., 1H NMR (300 MHz; DMSO-d6) 1.23 (s, 6 H); 1.28 (s, 6 H); 1.65 (s, 4 H); 2.02 (s, 3 H); 3.04 (t, J=7.1 Hz, 2 H); 3.81 (s, 3 H); 3.99 (t, J=7.1 Hz, 2 H); 7.04 (s, 1 H); 7.18–7.29 (m, 4 H); 7.36 (d, J=2.1 Hz, 1 H); 7.64 (dd, J1=9 Hz, J2=3.6 Hz, 1 H); 7.70 (t, J=3.7 Hz, 1 H); 7.91 (s, 1 H); 8.46 (d, J=4.0 Hz, 1 H).
Sources & evidence
- ORD record
- ord-5b4a3d696a6b428ba74a62ddda05b982
- Source dataset
- uspto-grants-2006_07
- Patent number
- US07071218B2
Reaction notes
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