Benzoyl chloride, 3,4,5-trimethoxy- → HCID 57991583, compound

HRID 556102Notes

Reaction equation

HRID 556102 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[N:10]=[C:11]([NH2:18])[S:12][C:13]=2[CH2:14][CH2:15][CH2:16][CH3:17])=[CH:5][CH:4]=1.[CH3:19][O:20][C:21]1[CH:22]=[C:23]([CH:27]=[C:28]([O:32][CH3:33])[C:29]=1[O:30][CH3:31])[C:24](Cl)=[O:25]>>[CH2:14]([C:13]1[S:12][C:11]([NH:18][C:24](=[O:25])[C:23]2[CH:22]=[C:21]([O:20][CH3:19])[C:29]([O:30][CH3:31])=[C:28]([O:32][CH3:33])[CH:27]=2)=[N:10][C:9]=1[C:6]1[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:8][CH:7]=1)[CH2:15][CH2:16][CH3:17]

Participants

3

Reactant 2

HCID 78282Benzoyl chloride, 3,4,5-trimethoxy-HCID 57991594HCID 57991594, compound

Product 1

HCID 57991583HCID 57991583, compoundYield 51.8%

Procedure

A procedure similar to that in Example 4 was used. 4-(4-methoxy-phenyl)-5-n-butyl-thiazol-2-ylamine prepared in Example 62 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 glassy crude product, 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 51.8%, mp: 197-198 └. 1H-NMR (CDCl3, 400 MHz) δ: 0.93 (3H, t, J=7.2 Hz, CH3), 1.43 (2H, sextuple, J=7.20 Hz, CH2), 1.72 (2H, quintuple, J=7.20 Hz, CH2), 2.88 (2H, t, J=7.2 Hz, CH3), 3.75 (6H, s, 2×OCH3), 3.78 (3H, s, OCH3), 3.89 (3H, s, OCH3), 6.74 (2H, d, J=8.80 Hz, ArH), 6.91 (2H, s, ArH), 7.28 (2H, d, J=8.80 Hz, ArH), 11.96 (1H, br, CONH); EI-MS m/e (%): 456.1 (M+, 49), 413.1 (7), 195.1 (100); HREI-MS Calcd. for C24H28N2O5S: 456.1719. found: 456.1718. Anal. Calcd. for C24H28N2O5S: C, 63.14; H, 6.18; N, 6.14. found: C, 63.24; H, 6.20; N, 6.25.

Workup

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

Sources & evidence

ORD record
ord-2f2acc23727e4727baf39cd8a7b11cab
Source dataset
uspto-grants-2011_11
Patent number
US08053581B2

Reaction notes

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