4-Fluorobenzoyl chloride → 4-fluoro-N-[4-(4-methoxy-phenyl)-5-(4-nitro-benzyl)-thiazol-2-yl]-benzamide

HRID 556043Notes

Reaction equation

HRID 556043 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[N:10]=[C:11]([NH2:24])[S:12][C:13]=2[CH2:14][C:15]2[CH:20]=[CH:19][C:18]([N+:21]([O-:23])=[O:22])=[CH:17][CH:16]=2)=[CH:5][CH:4]=1.[F:25][C:26]1[CH:34]=[CH:33][C:29]([C:30](Cl)=[O:31])=[CH:28][CH:27]=1>>[F:25][C:26]1[CH:34]=[CH:33][C:29]([C:30]([NH:24][C:11]2[S:12][C:13]([CH2:14][C:15]3[CH:20]=[CH:19][C:18]([N+:21]([O-:23])=[O:22])=[CH:17][CH:16]=3)=[C:9]([C:6]3[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=3)[N:10]=2)=[O:31])=[CH:28][CH:27]=1

Participants

3

Reactant 2

HCID 678794-Fluorobenzoyl chlorideHCID 579916084-(4-Methoxy-phenyl)-5-(4-nitro-benzyl)-thiazol-2-ylamine

Product 1

HCID 579916124-fluoro-N-[4-(4-methoxy-phenyl)-5-(4-nitro-benzyl)-thiazol-2-yl]-benzamideYield 81.3%

Procedure

A procedure similar to that in Example 4 was used. 4-(4-methoxy-phenyl)-5-(4-nitro-benzyl)-thiazol-2-ylamine prepared in Example 6 and p-fluorobenzoyl chloride were used as starting materials, allowed to react at 35-40° C. for 48 hours, 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 (4:1) to obtain a product as a yellow solid in a yield of 81.3%, mp: 188-189 └. 1H-NMR (CDCl3, 400 MHz) δ: 3.82 (3H, s, OCH3), 4.33 (2H, s, CH2), 6.87 (2H, d, J=8.68 Hz, ArH), 7.10 (2H, t, 3JFH=3JHH=8.68 Hz, ArH), 7.37 (2H, d, J=8.40 Hz, ArH), 7.39 (2H, d, J=8.68 Hz, ArH), 7.89 (2H, dd, 3JHH=8.68, 4JFH=5.02 Hz, ArH), 8.19 (2H, d, J=8.68 Hz, ArH); EI-MS m/e (%): 463.1 (M+, 60), 123.0 (100); HREI-MS Calcd. for C24H18FN3O4S: 463.1002. found: 463.1000. Anal. Calcd. for C24H18FN3O4S: C, 62.19; H, 3.91; N, 9.07. found: C, 62.21; H, 3.82; N, 9.02.

Workup

  1. customto react at 35-40° C. for 48 hours
  2. customto obtain a crude product, which
  3. customwas purified by a silica gel column chromatography
  4. washeluted with petroleum ether and ethyl acetate (4:1)

Sources & evidence

ORD record
ord-b8c07af43a3640ffaab9004f22921ed1
Source dataset
uspto-grants-2011_11
Patent number
US08053581B2

Reaction notes

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