Sodium hydride → HCID 20148591, compound

HRID 569064Notes

Reaction equation

HRID 569064 reaction equation
[S:1]1[C:5]2[C:6](=[O:10])[NH:7][CH:8]=[CH:9][C:4]=2[CH:3]=[CH:2]1.Cl.[CH3:12][N:13]([CH3:17])[CH2:14][CH2:15]Cl.[H-].[Na+]>CN(C)C=O.O>[CH3:12][N:13]([CH3:17])[CH2:14][CH2:15][N:7]1[CH:8]=[CH:9][C:4]2[CH:3]=[CH:2][S:1][C:5]=2[C:6]1=[O:10]

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 49833866H-thieno[2,3-c]pyridin-7-oneHCID 11636816N,N-Dimethylaminoethyl chloride hydrochloride2×

Product 1

HCID 20148591HCID 20148591, compoundYield 89%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of thieno[2,3-c]pyridin-7(6H)one (2.92 g, 19.3 mmol) in dry dimethylformamide (20 ml) under a nitrogen atmosphere was added 2-(dimethylamino)ethyl chloride hydrochloride (3.15 g, 21.8 mmol). This mixture was warmed to 80° C. and sodium hydride in mineral oil (60%, 2.6 g, 65 mmol) was added carefully and rapidly. After 1.5 hours additional 2-(dimethylamino)ethyl chloride hydrochloride (1.45 g, 10 mmol) was added. After two hours the reaction mixture was cooled and diluted with water. The crude product was extracted into chloroform and then into dilute hydrochloric acid. The acidic solution was made basic with sodium hydroxide and the product extracted into diethyl ether. This was dried over anhydrous sodium sulfate, filtered and evaporated to give an oily product (3.8 g, 89% yield) which contained less than 10% of the by-product resulting from O-alkylation.

Workup

  1. temperatureAfter two hours the reaction mixture was cooled
  2. extractionThe crude product was extracted into chloroform
  3. extractionthe product extracted into diethyl ether
  4. dry with materialThis was dried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-42f54be1b26841deac1ea44ae229a238
Source dataset
uspto-grants-1988_03
Patent number
US04731368

Reaction notes

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