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

HRID 556050Notes

Reaction equation

HRID 556050 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:27]=[C:28]([CH:32]=[C:33]([F:35])[CH:34]=1)[C:29](Cl)=[O:30]>>[F:25][C:26]1[CH:27]=[C:28]([CH:32]=[C:33]([F:35])[CH:34]=1)[C:29]([NH:24][C:11]1[S:12][C:13]([CH2:14][C:15]2[CH:20]=[CH:19][C:18]([N+:21]([O-:23])=[O:22])=[CH:17][CH:16]=2)=[C:9]([C:6]2[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=2)[N:10]=1)=[O:30]

Participants

3

Reactant 2

HCID 1456003,5-Difluorobenzoyl chlorideHCID 579916084-(4-Methoxy-phenyl)-5-(4-nitro-benzyl)-thiazol-2-ylamine

Product 1

HCID 579916243,5-difluoro-N-[4-(4-methoxy-phenyl)-5-(4-nitro-benzyl)-thiazol-2-yl]-benzamideYield 66.7%

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 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 66.7%, mp: 189-190└. 1H-NMR (CDCl3, 400 MHz) δ: 3.76 (3H, s, OCH3), 4.34 (2H, s, CH2), 6.72 (2H, d, J=8.68 Hz, ArH), 6.85 (1H, t, 3JFH=8.40 Hz, ArH), 7.18 (2H, d, 3JFH=5.32 Hz, ArH), 7.25 (2H, d, J=8.68 Hz, ArH), 7.40 (2H, d, J=8.40 Hz, ArH), 8.21 (2H, d, J=8.40 Hz, ArH), 12.05 (1H, br, CONH); EI-MS m/e (%): 481.1 (M+, 100), 141.0 (63); HREI-MS Calcd. for C24H17F2N3O4S: 481.0908. found: 481.0902. Anal. Calcd. for C24H17F2N3O4S: C, 59.87; H, 3.56; N, 8.73. found: C, 59.98; H, 3.80; N, 8.67.

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-0ec59929cc6d434f810e01b52c7bdb91
Source dataset
uspto-grants-2011_11
Patent number
US08053581B2

Reaction notes

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