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

HRID 556096Notes

Reaction equation

HRID 556096 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[N:10]=[C:11]([NH2:22])[S:12][C:13]=2[CH2:14][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[CH:5][CH:4]=1.[CH3:23][O:24][C:25]1[CH:26]=[C:27]([CH:31]=[C:32]([O:36][CH3:37])[C:33]=1[O:34][CH3:35])[C:28](Cl)=[O:29]>>[CH3:37][O:36][C:32]1[CH:31]=[C:27]([CH:26]=[C:25]([O:24][CH3:23])[C:33]=1[O:34][CH3:35])[C:28]([NH:22][C:11]1[S:12][C:13]([CH2:14][CH2:15][C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)=[C:9]([C:6]2[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:8][CH:7]=2)[N:10]=1)=[O:29]

Participants

3

Reactant 2

HCID 78282Benzoyl chloride, 3,4,5-trimethoxy-HCID 579916324-(4-Methoxy-phenyl)-5-phenylethyl-thiazol-2-ylamine

Product 1

HCID 579916473,4,5-trimethoxy-N-[4-(4-methoxy-phenyl)-5-phenylethyl-thiazol-2-yl]-benzamideYield 67.2%

Procedure

A procedure similar to that in Example 4 was used. 4-(4-methoxy-phenyl)-5-phenylethyl-thiazol-2-ylamine prepared in Example 57 and 3,4,5-trimethoxy-benzoyl chloride prepared in the step 1 of Example 37 were used as starting materials, allowed to react at room temperature overnight, followed by post-treatment to give a crude product as a foam, which was recrystallized with petroleum ether and ethyl acetate at a ratio of 2:1 (V:V) to obtain a product as a white solid in a yield of 67.2%, mp: 78-79 └. 1H-NMR (CDCl3, 400 MHz) δ: 3.03 (2H, t, J=7.60 Hz, CH2), 3.19 (2H, t, J=7.60 Hz, CH2), 3.80 (6H, s, 2×OCH3), 3.81 (3H, s, OCH3), 3.91 (3H, s, OCH3), 6.78 (2H, d, J=8.40 Hz, ArH), 7.02 (2H, s, ArH), 7.15˜7.32 (7H, m, ArH), 11.54 (1H, br, CONH); EI-MS m/e (%): 504.2 (M+, 24), 413.2 (53), 195.1 (100); HREI-MS Calcd. for C28H28N2O5S: 504.1719. found: 504.1716.

Workup

  1. customto react at room temperature overnight
  2. customto give a crude product as a foam, which
  3. customwas recrystallized with petroleum ether and ethyl acetate at a ratio of 2:1 (V:V)

Sources & evidence

ORD record
ord-4b6c008c07444abbbcf4ae394918beca
Source dataset
uspto-grants-2011_11
Patent number
US08053581B2

Reaction notes

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