Benzoyl chloride, 3,4,5-trimethoxy- → HCID 1349290, compound

HRID 556088Notes

Reaction equation

HRID 556088 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[N:10]=[C:11]([NH2:15])[S:12][C:13]=2[CH3:14])=[CH:5][CH:4]=1.[CH3:16][O:17][C:18]1[CH:19]=[C:20]([CH:24]=[C:25]([O:29][CH3:30])[C:26]=1[O:27][CH3:28])[C:21](Cl)=[O:22]>>[CH3:30][O:29][C:25]1[CH:24]=[C:20]([CH:19]=[C:18]([O:17][CH3:16])[C:26]=1[O:27][CH3:28])[C:21]([NH:15][C:11]1[S:12][C:13]([CH3:14])=[C:9]([C:6]2[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:8][CH:7]=2)[N:10]=1)=[O:22]

Participants

3

Reactant 2

HCID 78282Benzoyl chloride, 3,4,5-trimethoxy-HCID 6132284-(4-Methoxyphenyl)-5-methyl-1,3-thiazol-2(3H)-iminato

Product 1

HCID 1349290HCID 1349290, compoundYield 63%

Procedure

A procedure similar to that in Example 4 was used. 4-(4-methoxy-phenyl)-5-methyl-thiazol-2-ylamine prepared in Example 52 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, which was purified by a silica gel column chromatography eluted with a gradient of dichloromethane and ethyl acetate (15:1) to obtain a product as a white solid in a yield of 63.0%, mp: 105-106 └. 1H-NMR (CDCl3, 400 MHz) δ: 2.51 (3H, s, ArCH3), 3.78 (3H, s, OCH3), 3.79 (3H, s, OCH3), 3.80 (3H, s, OCH3), 3.89 (3H, s, OCH3), 6.78 (2H, d, J=8.44 Hz, ArH), 6.98 (2H, s, ArH), 7.35 (2H, d, J=8.44 Hz, ArH); EI-MS m/e (%): 414.1 (M+, 70), 195.1 (100); HREI-MS Calcd. for C21H22N2O5S: 414.1249. found: 414.1258.

Workup

  1. customto react at room temperature overnight
  2. customto give a crude product, which
  3. customwas purified by a silica gel column chromatography
  4. washeluted with a gradient of dichloromethane and ethyl acetate (15:1)

Sources & evidence

ORD record
ord-1f7e5824efb047278c5858383e675081
Source dataset
uspto-grants-2011_11
Patent number
US08053581B2

Reaction notes

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