Benzoyl chloride, 3,4,5-trimethoxy- → N-[5-benzyl-4-(4-methoxy-phenyl)-thiazol-2-yl]-3,4,5-trimethoxy-benzamide

HRID 556068Notes

Reaction equation

HRID 556068 reaction equation
[CH2:1]([C:8]1[S:12][C:11]([NH2:13])=[N:10][C:9]=1[C:14]1[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:22][O:23][C:24]1[CH:25]=[C:26]([CH:30]=[C:31]([O:35][CH3:36])[C:32]=1[O:33][CH3:34])[C:27](Cl)=[O:28]>>[CH2:1]([C:8]1[S:12][C:11]([NH:13][C:27](=[O:28])[C:26]2[CH:25]=[C:24]([O:23][CH3:22])[C:32]([O:33][CH3:34])=[C:31]([O:35][CH3:36])[CH:30]=2)=[N:10][C:9]=1[C:14]1[CH:15]=[CH:16][C:17]([O:20][CH3:21])=[CH:18][CH:19]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

3

Reactant 2

HCID 78282Benzoyl chloride, 3,4,5-trimethoxy-HCID 137372225-Benzyl-4-(4-methoxy-phenyl)-thiazol-2-ylamine

Product 1

HCID 57991634N-[5-benzyl-4-(4-methoxy-phenyl)-thiazol-2-yl]-3,4,5-trimethoxy-benzamideYield 61.7%

Procedure

A procedure similar to that in Example 4 was used. 5-benzyl-4-(4-methoxy-phenyl)-thiazol-2-ylamine prepared in Example 1 and 3,4,5-trimethoxy-benzoyl chloride prepared in the step 1 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 61.7%, mp: 157-158 └. 1H-NMR (CDCl3, 400 MHz) δ: 3.75 (6H, s, 2×OCH3), 3.77 (3H, s, OCH3), 3.87 (3H, s, OCH3), 4.21 (2H, s, CH2), 6.75 (2H, d, J=8.96 Hz, ArH), 6.92 (2H, s, ArH), 7.23˜7.35 (7H, m, ArH), 11.72 (1H, br, CONH); EI-MS m/e (%): 490.3 (M, 82), 195.1 (100); HREI-MS Calcd. for C27H26N2O5S: 490.1562. found: 490.1560.

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-d796a1de9f594a94a8d3c6eeef68b46a
Source dataset
uspto-grants-2011_11
Patent number
US08053581B2

Reaction notes

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