Water → HCID 70343912, compound

HRID 465355Notes

Reaction equation

HRID 465355 reaction equation
[CH3:1][O:2][C:3]1[C:19]([O:20][CH3:21])=[CH:18][CH:17]=[CH:16][C:4]=1[CH:5]=[CH:6][C:7]1[S:8][C:9]2[NH:10][CH2:11][CH2:12][CH2:13][C:14]=2[N:15]=1.C(=O)([O-])[O-].[K+].[K+].[ClH:28].[CH3:29][N:30]([CH2:32][CH2:33][Cl:34])[CH3:31].O>CN(C)C=O>[ClH:34].[ClH:28].[CH3:1][O:2][C:3]1[C:19]([O:20][CH3:21])=[CH:18][CH:17]=[CH:16][C:4]=1[CH:5]=[CH:6][C:7]1[S:8][C:9]2[N:10]([CH2:33][CH2:32][N:30]([CH3:31])[CH3:29])[CH2:11][CH2:12][CH2:13][C:14]=2[N:15]=1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 11636816N,N-Dimethylaminoethyl chloride hydrochlorideHCID 53812483HCID 53812483, compound

Product 1

HCID 70343912HCID 70343912, compoundYield 59.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

2-(2,3-Dimethoxystyryl)-4,5,6,7-tetrahydrothiazolo[5,4-b]pyridine (1.0 g, 3.3 mmole) and powdery potassium carbonate (1.37 g, 9.92 mmole) were suspended in dimethylformamide (20 ml). To the suspension was added N,N-dimethylaminoethyl chloride hydrochloride (0.57 g, 3.97 mmole) and the mixture was heated with stirring at 90° C. for 4 hours. Water was added to the mixture and an organic substance was extracted with a chloroform-methanol mixed solvent. The extract was dried over magnesium sulfate and concentrated. The residue was purified by flash column chromatography. The resulting oily compound was neutralized with hydrochloric acid and recrystallized from diethyl ether-ethanol to obtain the title compound (870 mg, yield: 54.4%).

Workup

  1. temperaturethe mixture was heated
  2. extractionan organic substance was extracted with a chloroform-methanol mixed solvent
  3. dry with materialThe extract was dried over magnesium sulfate
  4. concentrationconcentrated
  5. customThe residue was purified by flash column chromatography
  6. customrecrystallized from diethyl ether-ethanol

Sources & evidence

ORD record
ord-8a495654e7e648dcb172bdb84287ed10
Source dataset
uspto-grants-1992_10
Patent number
US05153201

Reaction notes

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