Veratroyl chloride → HCID 57991637, compound
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:25]=[C:26]([CH:30]=[CH:31][C:32]=1[O:33][CH3:34])[C:27](Cl)=[O:28]>>[CH2:1]([C:8]1[S:12][C:11]([NH:13][C:27](=[O:28])[C:26]2[CH:30]=[CH:31][C:32]([O:33][CH3:34])=[C:24]([O:23][CH3:22])[CH:25]=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 3,4-dimethoxy-benzoyl 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 petroleum ether and ethyl acetate (10:1) to obtain a product as a white solid in a yield of 46.5%, mp: 179-180└. 1H-NMR (CDCl3, 400 MHz) δ: 3.79 (3H, s, OCH3), 3.83 (3H, s, OCH3), 3.89 (3H, s, OCH3), 4.22 (2H, s, CH2), 6.73 (1H, d, J=8.40 Hz, ArH), 6.78 (2H, d, J=8.40 Hz, ArH), 7.26˜7.35 (9H, m, ArH), 11.03 (1H, br, CONH); EI-MS m/e (%): 460.1 (M+, 99), 164.9 (100); HREI-MS Calcd. for C26H24N2O4S: 460.1457. found: 460.1463. Anal. Calcd. for C26H24N2O4S: C, 67.81; H, 5.25; N, 6.08. found: C, 67.62; H, 5.20; N, 6.50.
Workup
- customto react at room temperature overnight
- customto obtain a crude product, which
- customwas purified by a silica gel column chromatography
- washeluted with petroleum ether and ethyl acetate (10:1)
Sources & evidence
- ORD record
- ord-80184cc1d289433785a746ed7c345e71
- Source dataset
- uspto-grants-2011_11
- Patent number
- US08053581B2
Reaction notes
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