Diethylaminoethyl chloride → HCID 20377683, compound

HRID 1703492Notes

Reaction equation

HRID 1703492 reaction equation
[CH2:1]([N:3]([CH2:7][CH3:8])[CH2:4][CH2:5]Cl)[CH3:2].[S:9]1[C:13]2[S:14][CH:15]=[CH:16][C:12]=2[CH:11]=[C:10]1[C:17]([C:19]1[CH:20]=[C:21]([CH:25]([CH3:29])[C:26]([O-:28])=[O:27])[CH:22]=[CH:23][CH:24]=1)=[O:18].[Na+]>CN(C)C=O.Cl>[S:9]1[C:13]2[S:14][CH:15]=[CH:16][C:12]=2[CH:11]=[C:10]1[C:17]([C:19]1[CH:20]=[C:21]([CH:25]([CH3:29])[C:26]([O:28][CH2:5][CH2:4][N:3]([CH2:1][CH3:2])[CH2:7][CH3:8])=[O:27])[CH:22]=[CH:23][CH:24]=1)=[O:18]

Participants

5

Reactant 2

HCID 13364Diethylaminoethyl chlorideHCID 23711741HCID 23711741, compound

Product 1

HCID 20377683HCID 20377683, compoundYield 108.1%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 6228DimethylformamideSolvent2×

Procedure

A solution of 2-diethylamino-chloroethane (1.6 g) in dimethylformamide (16 cc) is added dropwise to a suspension of sodium 2-{3-(thieno[2,3-b]thien-2-yl)carbonyl-phenyl}propionate (4 g) [prepared as described in Example 1] in dimethylformamide (16 cc). After 16 hours at 25° C., the reaction mixture is poured into distilled water (400 cc) and extracted three times with diethyl ether (total 300 cc). The combined ether phases are washed with a saturated aqueous sodium bicarbonate solution (75 cc), then three times with distilled water (total 300 cc), dried over anhydrous sodium sulphate in the presence of decolourizing charcoal (0.5 g), filtered and evaporated. The residue obtained (4.75 g), to which is added some product (3.1 g) prepared in the same way, is dissolved in 1N aqueous hydrochloric acid (50 cc). The solution is washed three times with diethyl ether (total 175 cc) and then rendered alkaline to pH 11 by the addition of 1N aqueous sodium hydroxide solution (55 cc). The resulting precipitate is extracted three times with diethyl ether (175 cc). The combined ether solutions are washed three times with distilled water (total 175 cc), dried over anhydrous sodium sulphate in the presence of decolourizing charcoal (0.5 g), filtered and evaporated. 2-Diethylaminoethyl 2-{3-(thieno[2,3-b]thien-2-yl)carbonyl-phenyl}propionate (5.3 g), in the form of an oil, is thus obtained.

Workup

  1. additionthe reaction mixture is poured
  2. distillationinto distilled water (400 cc)
  3. extractionextracted three times with diethyl ether (total 300 cc)
  4. washThe combined ether phases are washed with a saturated aqueous sodium bicarbonate solution (75 cc)
  5. dry with materialthree times with distilled water (total 300 cc), dried over anhydrous sodium sulphate in the presence of decolourizing charcoal (0.5 g)
  6. filtrationfiltered
  7. customevaporated
  8. customThe residue obtained (4.75 g)
  9. customprepared in the same way
  10. washThe solution is washed three times with diethyl ether (total 175 cc)
  11. additionby the addition of 1N aqueous sodium hydroxide solution (55 cc)
  12. extractionThe resulting precipitate is extracted three times with diethyl ether (175 cc)
  13. washThe combined ether solutions are washed three times with distilled water (total 175 cc)
  14. dry with materialdried over anhydrous sodium sulphate in the presence of decolourizing charcoal (0.5 g)
  15. filtrationfiltered
  16. customevaporated

Sources & evidence

ORD record
ord-372dde4bad7c40259382a6c5655e0610
Source dataset
uspto-grants-1978_11
Patent number
US04124596

Reaction notes

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