3,5-Difluorobenzoyl chloride → 3,5-difluoro-N-[4-(4-fluoro-phenyl)-5-(4-nitro-benzyl)-thiazol-2-yl]-benzamide

HRID 556051Notes

Reaction equation

HRID 556051 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:26]=[C:27]([CH:31]=[C:32]([F:34])[CH:33]=1)[C:28](Cl)=[O:29]>>[F:24][C:25]1[CH:26]=[C:27]([CH:31]=[C:32]([F:34])[CH:33]=1)[C:28]([NH:23][C:10]1[S:11][C:12]([CH2:13][C:14]2[CH:19]=[CH:18][C:17]([N+:20]([O-:22])=[O:21])=[CH:16][CH:15]=2)=[C:8]([C:5]2[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=2)[N:9]=1)=[O:29]

Participants

3

Reactant 2

HCID 1456003,5-Difluorobenzoyl chlorideHCID 579916194-(4-Fluoro-phenyl)-5-(4-nitro-benzyl)-thiazol-2-ylamine

Product 1

HCID 579916233,5-difluoro-N-[4-(4-fluoro-phenyl)-5-(4-nitro-benzyl)-thiazol-2-yl]-benzamideYield 58%

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 3,5-difluorobenzoyl chloride prepared in the step 1 of Example 16 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 a gradient of dichloromethane and ethyl acetate (20:1-10:1) to obtain a product as a white solid in a yield of 58.0%, mp: 216-218 └. 1H-NMR (DMSO-d6, 400 MHz) δ: 4.44 (2H, s, CH2), 7.30 (2H, t, 3JFH=3JHH=8.96 Hz, ArH), 7.51 (2H, d, J=8.68 Hz, ArH), 7.30 (1H, t, 3JFH=9.00 Hz, ArH), 7.68 (2H, dd, 3JHH=8.68 Hz, 4JFH=5.60 Hz, ArH), 7.30 (2H, d, 3JFH=6.16 Hz, ArH), 8.20 (2H, d, J=8.68 Hz, ArH), 12.95 (1H, br, CONH); EI-MS m/e (%): 469.1 (M+, 77), 141.1 (100); HREI-MS Calcd. for C23H14F3N3O3S: 469.0708. found: 469.0710. Anal. Calcd. for C23H14F3N3O3S: C, 58.85; H, 3.01; N, 8.95. found: C, 58.42; H, 2.64; N, 8.80.

Workup

  1. customto react at room temperature overnight
  2. customto obtain a crude product, which
  3. customwas purified by a silica gel column chromatography
  4. washeluted with a gradient of dichloromethane and ethyl acetate (20:1-10:1)

Sources & evidence

ORD record
ord-65d244fb2c81462ea2447218602dbb84
Source dataset
uspto-grants-2011_11
Patent number
US08053581B2

Reaction notes

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