Veratroyl chloride → HCID 57991648, compound
Reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[N:10]=[C:11]([NH2:18])[S:12][C:13]=2[CH2:14][CH2:15][CH2:16][CH3:17])=[CH:5][CH:4]=1.[CH3:19][O:20][C:21]1[CH:22]=[C:23]([CH:27]=[CH:28][C:29]=1[O:30][CH3:31])[C:24](Cl)=[O:25]>>[CH2:14]([C:13]1[S:12][C:11]([NH:18][C:24](=[O:25])[C:23]2[CH:27]=[CH:28][C:29]([O:30][CH3:31])=[C:21]([O:20][CH3:19])[CH:22]=2)=[N:10][C:9]=1[C:6]1[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:8][CH:7]=1)[CH2:15][CH2:16][CH3:17]Participants
Procedure
A procedure similar to that in Example 4 was used. 4-(4-methoxy-phenyl)-5-n-butyl-thiazol-2-ylamine prepared in Example 62 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 62.8%, mp: 150-151 └. 1H-NMR (CDCl3, 400 MHz) δ: 0.93 (3H, t, J=7.2 Hz, CH3), 1.41 (2H, sextuple, J=7.20 Hz, CH2), 1.72 (2H, quintuple, J=7.20 Hz, CH2), 2.88 (2H, t, J=7.2 Hz, CH3), 3.80 (3H, s, OCH3), 3.83 (3H, s, OCH3), 3.94 (3H, s, OCH3), 6.72˜6.82 (3H, m, ArH), 7.25˜7.40 (4H, m, ArH), 11.16 (1H, br, CONH); EI-MS m/e (%): 426.1 (M+, 50), 383.1 (7), 165.1 (100); HREI-MS Calcd. for C23H26N2O4S: 426.1613. found: 426.1613. Anal. Calcd. for C23H26N2O4S: C, 64.77; H, 6.14; N, 6.57. found: C, 64.56; H, 6.23; N, 6.61.
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-487da6239e004ac389577a50b4d312ed
- Source dataset
- uspto-grants-2011_11
- Patent number
- US08053581B2
Reaction notes
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