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

HRID 556044Notes

Reaction equation

HRID 556044 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.[F:24][C:25]1[CH:33]=[CH:32][C:28]([C:29](Cl)=[O:30])=[CH:27][CH:26]=1>>[F:24][C:25]1[CH:33]=[CH:32][C:28]([C:29]([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:30])=[CH:27][CH:26]=1

Participants

3

Reactant 2

HCID 678794-Fluorobenzoyl chlorideHCID 579916194-(4-Fluoro-phenyl)-5-(4-nitro-benzyl)-thiazol-2-ylamine

Product 1

HCID 579916444-fluoro-N-[4-(4-fluoro-phenyl)-5-(4-nitro-benzyl)-thiazol-2-yl]-benzamideYield 69.6%

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-fluorobenzoyl chloride were used as starting materials, allowed to react at 35-40° C. for 24 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 pale yellow solid in a yield of 69.6%, mp: 120-122 └. 1H-NMR (CDCl3, 400 MHz) δ: 4.33 (2H, s, CH2), 7.12 (2H, t, 3JFH=3JHH=8.44 Hz, ArH), 7.18 (2H, t, 3JFH=3JHH=8.40 Hz, ArH), 7.38 (2H, d, J=8.68 Hz, ArH), 7.49 (2H, dd, 3JHH=8.72, 4JFH=5.32 Hz, ArH), 7.99 (2H, dd, 3JHH=8.96, 4JFH=5.32 Hz, ArH); 8.20 (2H, d, J=8.68 Hz, ArH); EI-MS m/e (%): 451.0 (M+, 32), 123.0 (100); HREI-MS Calcd. for C23H15F2N3O3S: 451.0802. found: 451.0818. Anal. Calcd. for C23H15F2N3O3S: C, 61.19; H, 3.35; N, 9.31. found: C, 61.16; H, 3.08; N, 9.35.

Workup

  1. customto react at 35-40° C. for 24 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-5107d97727c544d5a00ba558fffb1702
Source dataset
uspto-grants-2011_11
Patent number
US08053581B2

Reaction notes

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