3,5-Dimethoxybenzoyl chloride → HCID 57991577, compound

HRID 556074Notes

Reaction equation

HRID 556074 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:33][CH3:34])[CH:32]=1)[C:27](Cl)=[O:28]>>[CH2:1]([C:8]1[S:12][C:11]([NH:13][C:27](=[O:28])[C:26]2[CH:30]=[C:31]([O:33][CH3:34])[CH:32]=[C:24]([O:23][CH3:22])[CH:25]=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 870033,5-Dimethoxybenzoyl chlorideHCID 137372225-Benzyl-4-(4-methoxy-phenyl)-thiazol-2-ylamine

Product 1

HCID 57991577HCID 57991577, compoundYield 65.7%

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 3,5-dimethoxy-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 65.7%, mp: 152-153 └. 1H-NMR (CDCl3, 400 MHz) δ: 3.78 (6H, s, 2×OCH3), 3.80 (3H, s, OCH3), 4.22 (2H, s, CH2), 6.55 (1H, t, J=2.12 Hz, ArH), 6.83 (2H, d, J=8.68 Hz, ArH), 6.90 (2H, t, J=2.12 Hz, ArH), 7.25˜7.33 (5H, m, ArH), 7.39 (2H, d, J=8.68 Hz, ArH), 10.75 (1H, br, CONH); EI-MS m/e (%): 460.2 (M+, 100), 165.0 (84); HREI-MS Calcd. for C26H24N2O4S: 460.1457. found: 460.1464.

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-a77f5e03e9f84d20b120247f74edab90
Source dataset
uspto-grants-2011_11
Patent number
US08053581B2

Reaction notes

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