Veratroyl chloride → 3,4-dimethoxy-N-[4-(4-methoxy-phenyl)-5-phenylethyl-thiazol-2-yl]-benzamide
Reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[N:10]=[C:11]([NH2:22])[S:12][C:13]=2[CH2:14][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[CH:5][CH:4]=1.[CH3:23][O:24][C:25]1[CH:26]=[C:27]([CH:31]=[CH:32][C:33]=1[O:34][CH3:35])[C:28](Cl)=[O:29]>>[CH3:23][O:24][C:25]1[CH:26]=[C:27]([CH:31]=[CH:32][C:33]=1[O:34][CH3:35])[C:28]([NH:22][C:11]1[S:12][C:13]([CH2:14][CH2:15][C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)=[C:9]([C:6]2[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:8][CH:7]=2)[N:10]=1)=[O:29]Participants
Procedure
A procedure similar to that in Example 4 was used. 4-(4-methoxy-phenyl)-5-phenylethyl-thiazol-2-ylamine prepared in Example 57 and 3,4-dimethoxy-benzoyl chloride prepared in the step 1 of Example 12 were used as starting materials, allowed to react at room temperature overnight, followed by post-treatment to give a crude product, which was recrystallized with petroleum ether and ethyl acetate at a ratio of 2:1 (V:V) to obtain a product as a white solid in a yield of 76.4%, mp: 74-75 └. 1H-NMR (CDCl3, 400 MHz) δ: 3.02 (2H, t, J=7.60 Hz, CH2), 3.19 (2H, t, J=7.60 Hz, CH2), 3.83 (3H, s, OCH3), 3.94 (3H, s, OCH3), 3.96 (3H, s, OCH3), 9.85˜7.95 (3H, m, ArH), 7.15˜7.37 (7H, m, ArH), 7.51 (2H, s, ArH), 10.48 (1H, br, CONH); EI-MS m/e (%): 474.1 (M+, 21), 383.0 (58), 165.0 (100); HREI-MS Calcd. for C27H26N2O4S: 474.1613. found: 474.1613.
Workup
- customto react at room temperature overnight
- customto give a crude product, which
- customwas recrystallized with petroleum ether and ethyl acetate at a ratio of 2:1 (V:V)
Sources & evidence
- ORD record
- ord-32ed6fcff0f94ffbae9c7b9cd7f66939
- Source dataset
- uspto-grants-2011_11
- Patent number
- US08053581B2
Reaction notes
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