4-Cyanobenzoyl chloride → 4-cyano-N-[4-(4-fluoro-phenyl)-5-(4-nitro-benzyl)-thiazol-2-yl]-benzamide
Reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]=[C:10]([NH2:23])[S:11][C:12]=2[CH2:13][C:14]2[CH:19]=[CH:18][C:17]([N+:20]([O-:22])=[O:21])=[CH:16][CH:15]=2)=[CH:4][CH:3]=1.[C:24]([C:26]1[CH:34]=[CH:33][C:29]([C:30](Cl)=[O:31])=[CH:28][CH:27]=1)#[N:25]>>[C:24]([C:26]1[CH:34]=[CH:33][C:29]([C:30]([NH:23][C:10]2[S:11][C:12]([CH2:13][C:14]3[CH:19]=[CH:18][C:17]([N+:20]([O-:22])=[O:21])=[CH:16][CH:15]=3)=[C:8]([C:5]3[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=3)[N:9]=2)=[O:31])=[CH:28][CH:27]=1)#[N:25]Participants
Procedure
A procedure similar to that in Example 4 was used. 4-(4-fluoro-phenyl)-5-(4-nitro-benzyl)-thiazol-2-ylamine prepared in Example 9 and p-cyanobenzoyl chloride prepared in the step 1 of Example 13 were used as starting materials, allowed to react at room temperature overnight, followed by post-treatment to obtain a crude product, which was recrystallized with a solvent mixture of ethyl acetate and petroleum ether to obtain a product as a off-white solid in a yield of 62.9%, mp: 244-245└. 1H-NMR (CDCl3, 400 MHz) δ: 4.33 (2H, s, CH2), 7.07 (2H, t, 3JFH=3JHH=8.44 Hz, ArH), 7.38 (2H, d, J=8.40 Hz, ArH), 7.43 (2H, dd, 3JHH=8.72, 4JFH=5.32 Hz, ArH), 7.75 (2H, d, J=7.84 Hz, ArH), 7.98 (2H, d, J=8.12 Hz, ArH), 8.20 (2H, d, J=8.40 Hz, ArH); EI-MS m/e (%): 458.3 (M+, 79), 129.9 (100); HREI-MS Calcd. for C24H15FN4O3S: 458.0849. found: 458.0850. Anal. Calcd. for C24H15FN4O3S: C, 62.88; H, 3.30; N, 12.22. found: C, 62.52; H, 2.96; N, 12.04.
Workup
- customto react at room temperature overnight
- customto obtain a crude product, which
- customwas recrystallized with a solvent mixture of ethyl acetate and petroleum ether
Sources & evidence
- ORD record
- ord-911fd4a2b71e4674bb3767a5d0f6e8a4
- Source dataset
- uspto-grants-2011_11
- Patent number
- US08053581B2
Reaction notes
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