p-Anisoyl chloride → N-[5-benzyl-4-(4-methoxy-phenyl)-thiazol-2-yl]-4-methoxy-benzamide
Reaction equation
[CH2:1]([C:8]1[S:12][C:11]([NH2:13])=[N:10][C:9]=1[C:14]1[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:22][O:23][C:24]1[CH:32]=[CH:31][C:27]([C:28](Cl)=[O:29])=[CH:26][CH:25]=1>>[CH2:1]([C:8]1[S:12][C:11]([NH:13][C:28](=[O:29])[C:27]2[CH:31]=[CH:32][C:24]([O:23][CH3:22])=[CH:25][CH:26]=2)=[N:10][C:9]=1[C:14]1[CH:15]=[CH:16][C:17]([O:20][CH3:21])=[CH:18][CH:19]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1Participants
Procedure
A procedure similar to that in Example 4 was used. 5-benzyl-4-(4-methoxy-phenyl)-thiazol-2-ylamine prepared in Example 1 and p-methoxybenzoyl chloride prepared in the step 1 were used as starting materials, allowed to react at room temperature overnight, followed by post-treatment to obtain a crude product, which was purified by a silica gel column chromatography eluted with a gradient of dichloromethane and ethyl acetate (100:0-10:1) to obtain a product as a white solid in a yield of 58.7%, mp: 58-59 └. 1H-NMR (CDCl3, 400 MHz) δ: 3.73 (3H, s, OCH3), 3.85 (3H, s, OCH3), 4.22 (2H, s, CH2), 6.89 (4H, t, J=8.44 Hz, ArH), 7.22˜7.35 (5H, m, ArH), 7.45 (2H, t, J=8.68 Hz, ArH), 7.82 (2H, t, J=8.68 Hz, ArH), 10.27 (1H, br, CONH); EI-MS m/e (%): 430.1 (M, 89), 135.0 (100); HREI-MS Calcd. for C25H22N2O3S: 430.1351. found: 430.1361.
Workup
- customto react at room temperature overnight
- customto obtain a crude product, which
- customwas purified by a silica gel column chromatography
- washeluted with a gradient of dichloromethane and ethyl acetate (100:0-10:1)
Sources & evidence
- ORD record
- ord-1bf3a767dbcc4d29ad6ba9045e803f4f
- Source dataset
- uspto-grants-2011_11
- Patent number
- US08053581B2
Reaction notes
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