2-Methoxybenzoyl chloride → N-[5-benzyl-4-(4-methoxy-phenyl)-thiazol-2-yl]-2-methoxy-benzamide

HRID 556067Notes

Reaction equation

HRID 556067 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:32]=[CH:31][CH:30]=[CH:29][C:25]=1[C:26](Cl)=[O:27]>>[CH2:1]([C:8]1[S:12][C:11]([NH:13][C:26](=[O:27])[C:25]2[CH:29]=[CH:30][CH:31]=[CH:32][C:24]=2[O:23][CH3:22])=[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 889692-Methoxybenzoyl chlorideHCID 137372225-Benzyl-4-(4-methoxy-phenyl)-thiazol-2-ylamine

Product 1

HCID 57991615N-[5-benzyl-4-(4-methoxy-phenyl)-thiazol-2-yl]-2-methoxy-benzamideYield 65.6%

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 o-methoxybenzoyl 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 65.6%, mp: 147-148└. 1H-NMR (CDCl3, 400 MHz) δ: 3.84 (3H, s, OCH3), 4.09 (3H, s, OCH3), 4.21 (2H, s, CH2), 6.97 (2H, d, J=8.68 Hz, ArH), 7.05 (1H, d, J=8.12 Hz, ArH), 7.14 (1H, t, J=8.12 Hz, ArH), 7.22˜7.32 (5H, m, ArH), 7.53˜7.56 (3H, m, ArH), 8.28 (1H, dd, J=7.84 Hz, 1.68 Hz, ArH), 11.05 (1H, br, CONH); EI-MS m/e (%): 430.2 (M+, 89), 135.1 (100); HREI-MS Calcd. for C25H22N2O3S: 430.1351. found: 430.1357.

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-4841133510e546f9b23de7a365282c94
Source dataset
uspto-grants-2011_11
Patent number
US08053581B2

Reaction notes

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