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

HRID 556059Notes

Reaction equation

HRID 556059 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.[CH3:25][O:26][C:27]1[CH:28]=[C:29]([CH:33]=[CH:34][C:35]=1[O:36][CH3:37])[C:30](Cl)=[O:31]>>[CH3:25][O:26][C:27]1[CH:28]=[C:29]([CH:33]=[CH:34][C:35]=1[O:36][CH3:37])[C:30]([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:31]

Participants

3

Reactant 2

HCID 77070Veratroyl chlorideHCID 579916084-(4-Methoxy-phenyl)-5-(4-nitro-benzyl)-thiazol-2-ylamine

Product 1

HCID 579915963,4-dimethoxy-N-[4-(4-methoxy-phenyl)-5-(4-nitro-benzyl)-thiazol-2-yl]-benzamideYield 60.8%

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 3,4-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 (100:0-10:1) to obtain a product as a white solid in a yield of 60.8%, mp: 106-108└. 1H-NMR (CDCl3, 400 MHz) δ: 3.83 (3H, s, OCH3), 3.92 (3H, s, OCH3), 3.97 (3H, s, OCH3), 4.33 (2H, s, CH2), 6.85˜6.89 (3H, m, ArH), 7.37˜7.45 (6H, m, ArH), 8.18 (2H, t, J=8.68 Hz, ArH), 10.48 (1H, br, CONH, exchangable); EI-MS m/e (%): 505.0 (M+, 54), 165.0 (100); HREI-MS Calcd. for C26H23N3O6S: 505.1308. found: 505.1315. Anal. Calcd. for C26H23N3O6S: C, 61.77; H, 4.59; N, 8.31. found: C, 61.90; H, 4.70; N, 8.05.

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 (100:0-10:1)

Sources & evidence

ORD record
ord-7e6e003c19384ae8a2e6d5d9092b17d1
Source dataset
uspto-grants-2011_11
Patent number
US08053581B2

Reaction notes

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