N,N-Dimethylethylenediamine → HCID 54311990, compound

HRID 1703493Notes

Reaction equation

HRID 1703493 reaction equation
[S:1]1[C:5]2[S:6][CH:7]=[CH:8][C:4]=2[CH:3]=[C:2]1[C:9]([C:11]1[CH:12]=[C:13]([CH:17]([CH3:21])[C:18]([OH:20])=O)[CH:14]=[CH:15][CH:16]=1)=[O:10].[CH3:22][N:23]([CH3:27])[CH2:24][CH2:25][NH2:26]>C(OCC)C.Cl>[CH3:22][N:23]([CH3:27])[CH2:24][CH2:25][NH:26][C:18](=[O:20])[CH:17]([C:13]1[CH:14]=[CH:15][CH:16]=[C:11]([C:9]([C:2]2[S:1][C:5]3[S:6][CH:7]=[CH:8][C:4]=3[CH:3]=2)=[O:10])[CH:12]=1)[CH3:21]

Participants

5

Reactant 2

HCID 66053N,N-DimethylethylenediamineHCID 20377675HCID 20377675, compound

Product 1

HCID 54311990HCID 54311990, compoundYield 37.3%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 3283Diethyl EtherSolvent2×

Procedure

N,N'-Carbonyldiimidazole (3.8 g) is added to 2-{3-(thieno[2,3-b]thien-2-yl)carbonyl-phenyl}propionic acid (7.25 g) [prepared as described in a previous Example] in solution in diethyl ether (70 cc). When the evolution of gas has ceased, 2-dimethylaminoethylamine (2.1 g) in solution in diethyl ether (25 cc) is then added. After 20 hours at 25° C., the reaction mixture is evaporated. The residue, dissolved in methylene chloride (100 cc), is washed four times with a 5% (w/v) aqueous sodium chloride solution (total 400 cc), dried over anhydrous sodium sulphate in the presence of decolourizing charcoal (0.5 g), filtered and evaporated. The oil obtained (5.4 g) is dissolved in N aqueous hydrochloric acid solution (50 cc). This solution is washed three times with diethyl ether (total 150 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 methylene chloride (total 150 cc). The combined methylene chloride solutions are washed three times with distilled water (total 150 cc), dried over anhydrous sodium sulphate in the presence of decolourizing charcoal (0.5 g), filtered and evaporated. N-(2-Dimethylaminoethyl) 2-{3-(thieno-[2,3-b]thien-2-yl)carbonyl-phenyl}propionamide (3.3 g), in the form of an oil, is thus obtained.

Workup

  1. customprepared
  2. customthe reaction mixture is evaporated
  3. dissolutionThe residue, dissolved in methylene chloride (100 cc)
  4. washis washed four times with a 5% (w/v) aqueous sodium chloride solution (total 400 cc)
  5. dry with materialdried over anhydrous sodium sulphate in the presence of decolourizing charcoal (0.5 g)
  6. filtrationfiltered
  7. customevaporated
  8. customThe oil obtained (5.4 g)
  9. washThis solution is washed three times with diethyl ether (total 150 cc)
  10. additionby the addition of 1N aqueous sodium hydroxide solution (55 cc)
  11. extractionThe resulting precipitate is extracted three times with methylene chloride (total 150 cc)
  12. washThe combined methylene chloride solutions are washed three times with distilled water (total 150 cc)
  13. dry with materialdried over anhydrous sodium sulphate in the presence of decolourizing charcoal (0.5 g)
  14. filtrationfiltered
  15. customevaporated

Sources & evidence

ORD record
ord-0612477ebe3046c695a66fc5ce24caca
Source dataset
uspto-grants-1978_11
Patent number
US04124596

Reaction notes

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