Dimethylamine → HCID 19041005, compound

HRID 1683802Notes

Reaction equation

HRID 1683802 reaction equation
[CH3:1][NH:2][CH3:3].[CH2:4]([O:6][C:7]1[CH:8]=[C:9]([C:16]2[S:17][CH:18]=[C:19]([C:21]3[CH:26]=[CH:25][CH:24]=[C:23]([CH:27]4[CH2:29][O:28]4)[N:22]=3)[N:20]=2)[CH:10]=[CH:11][C:12]=1[O:13][CH2:14][CH3:15])[CH3:5]>CO>[CH2:4]([O:6][C:7]1[CH:8]=[C:9]([C:16]2[S:17][CH:18]=[C:19]([C:21]3[CH:26]=[CH:25][CH:24]=[C:23]([CH:27]([OH:28])[CH2:29][N:2]([CH3:3])[CH3:1])[N:22]=3)[N:20]=2)[CH:10]=[CH:11][C:12]=1[O:13][CH2:14][CH3:15])[CH3:5]

Participants

4

Reactant 2

HCID 674DimethylamineHCID 19041129HCID 19041129, compound

Product 1

HCID 19041005HCID 19041005, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

2.4 g of a 50% aqueous dimethylamine solution was added to a solution of 1 g of 2-(3,4-diethoxyphenyl)-4-(6-oxiranyl-2-pyridyl)thiazole dissolved in 200 ml of methanol. The mixture was refluxed overnight. The resulting precipitate was removed by filtration. The filtrate was concentrated. The concentrate was purified by silica gel column chromatography (elutant: dichloromethane/methanol=20/1) and silica gel thin-layer chromatography and then recrystallized from diethyl ether-dichloromethane to obtain 140 mg of 2-(3,4-diethoxyphenyl)-4-[6-(1-hydroxy-2-dimethylaminoethyl)-2-pyridyl]thiazole (A). Further, recrystallization from diethyl ether-n-hexane was conducted to obtain 28 mg of 2-(3,4-diethoxyphenyl)-4-[6-(1-dimethylamino-2-hydroxyethyl)-2-pyridyl]thiazole (B).

Workup

  1. temperatureThe mixture was refluxed overnight
  2. customThe resulting precipitate was removed by filtration
  3. concentrationThe filtrate was concentrated
  4. customThe concentrate was purified by silica gel column chromatography (elutant: dichloromethane/methanol=20/1) and silica gel thin-layer chromatography
  5. customrecrystallized from diethyl ether-dichloromethane

Sources & evidence

ORD record
ord-c0d2d1f0a9994f549803a545388703aa
Source dataset
uspto-grants-1997_06
Patent number
US05639770

Reaction notes

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