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

HRID 556052Notes

Reaction equation

HRID 556052 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.[CH3:24][O:25][C:26]1[CH:27]=[C:28]([CH:32]=[CH:33][C:34]=1[O:35][CH3:36])[C:29](Cl)=[O:30]>>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[N:9]=[C:10]([NH:23][C:29](=[O:30])[C:28]3[CH:32]=[CH:33][C:34]([O:35][CH3:36])=[C:26]([O:25][CH3:24])[CH:27]=3)[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:6][CH:7]=1

Participants

3

Reactant 2

HCID 77070Veratroyl chlorideHCID 579916194-(4-Fluoro-phenyl)-5-(4-nitro-benzyl)-thiazol-2-ylamine

Product 1

HCID 57991645N-[4-(4-fluoro-phenyl)-5-(4-nitro-benzyl)-thiazol-2-yl]-3,4-dimethoxy-benzamideYield 24%

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 3,4-dimethoxy-benzoyl chloride prepared in the step 1 of Example 12 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 24.0%, mp: 128-129└. 1H-NMR (DMSO-d6, 400 MHz) δ: 3.91 (3H, s, OCH3), 3.95 (3H, s, OCH3), 4.31 (2H, s, CH2), 6.90 (1H, d, J=9.00 Hz, ArH), 7.08 (2H, t, J=8.68 Hz, ArH), 7.38 (2H, d, J=8.68 Hz, ArH), 7.25˜7.47 (4H, m, ArH), 8.19 (2H, d, J=8.68 Hz, ArH), 10.04 (1H, br, CONH); EI-MS m/e (%): 493.2 (M+, 17), 165.3 (100); HREI-MS Calcd. for C25H20FN3O5S: 493.1108. found: 493.1105.

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-4631e895c6bb4be8804e814c4ad0c73e
Source dataset
uspto-grants-2011_11
Patent number
US08053581B2

Reaction notes

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