2,4-Dimethoxybenzoyl chloride → HCID 57991601, compound

HRID 556066Notes

Reaction equation

HRID 556066 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]=[C:31]([O:33][CH3:34])[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][C:31]([O:33][CH3:34])=[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 27347192,4-Dimethoxybenzoyl chlorideHCID 137372225-Benzyl-4-(4-methoxy-phenyl)-thiazol-2-ylamine

Product 1

HCID 57991601HCID 57991601, compoundYield 71%

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 2,4-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 71.0%, mp: 196-197 └. 1H-NMR (CDCl3, 400 MHz) δ: 3.85 (3H, s, OCH3), 3.88 (3H, s, OCH3), 4.08 (3H, s, OCH3), 4.20 (2H, s, CH2), 6.54 (1H, d, J=2.24 Hz, ArH), 6.65 (1H, dd, J=8.96 Hz, 2.24 Hz, ArH), 6.97 (2H, d, J=8.96 Hz, ArH), 7.22˜7.34 (5H, m, ArH), 7.56 (2H, d, J=8.96 Hz, ArH), 8.22 (1H, d, J=8.68 Hz, ArH), 11.01 (1H, br, CONH); EI-MS m/e (%): 460.1 (M+, 58), 165.0 (100); HREI-MS Calcd. for C26H24N2O4S: 460.1457. found: 460.1454. Anal. Calcd. for C26H24N2O4S: C, 67.81; H, 5.25; N, 6.08. found: C, 68.04; H, 5.16; N, 6.19.

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-404740667df3438caa05c22066570bae
Source dataset
uspto-grants-2011_11
Patent number
US08053581B2

Reaction notes

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