Ethanol → [2-(2-Thienyl)ethylamino](2-chlorophenyl)acetonitrile

HRID 1384469Notes

Reaction equation

HRID 1384469 reaction equation
S(=O)(O)[O-].[Na+].C(O)C.[Cl:9][C:10]1[CH:17]=[CH:16][CH:15]=[CH:14][C:11]=1[CH:12]=O.[S:18]1[CH:22]=[CH:21][CH:20]=[C:19]1[CH2:23][CH2:24][NH2:25].[C-:26]#[N:27].[Na+]>O>[S:18]1[CH:22]=[CH:21][CH:20]=[C:19]1[CH2:23][CH2:24][NH:25][CH:12]([C:11]1[CH:14]=[CH:15][CH:16]=[CH:17][C:10]=1[Cl:9])[C:26]#[N:27]

Participants

7

Reactant 5

HCID 702EthanolHCID 69962-ChlorobenzaldehydeHCID 8929Sodium CyanideHCID 116521ThiopheneethanamineHCID 23665763Sodium Bisulfite

Product 1

HCID 10858772[2-(2-Thienyl)ethylamino](2-chlorophenyl)acetonitrile

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Conditions

Temperature
40 °C

Procedure

104 g (1 mol) of sodium bisulfite is dissolved in the mixture of 900 ml of water and 250 mol of ethanol and to the solution 140.6 g (1 mol) o-chlorobenzaldehyde is added. After a few minutes the aldehyde bisulfite adduct precipitates in the form of white crystals, while the temperature increases to 40° C. After 1 hour of stirring 127.2 g (1 mol) of 2-(2-thienyl)ethylamine is added to the reaction mixture, then it was stirred at 50° C. for 2 hours. During this time the crystalline aldehyde bisulfite transforms into an oily material. The mixture is cooled to room temperature and the solution of 49 g (1 mol) of sodium cyanide in 100 ml of water is added to it. During the addition, the temperature of the reaction mixture increases to 40° C. The mixture is then stirred at 60° C. Till the reaction is completed (1 hour). The oily organic phase is then extracted with 400 ml of 1,2-dichloroethane, washed to cyanide-free with 2×200 ml of water. Traces of 2-(2-thienyl)ethylamine are removed by treatment with 100 ml of 3% hydrochloric acid solution. The dichloroethane phase was dried over anhydrous sodium sulfate and evaporated in vacuo. The residual fast crystallizing oil is the product. Weight: 260 g (94%) mp.: 40-41° C. The product was identified by elemental analysis, IR spectrum and 1H-NMR investigation.

Workup

  1. additionis added
  2. customAfter a few minutes the aldehyde bisulfite adduct precipitates in the form of white crystals, while the temperature
  3. additionis added to the reaction mixture
  4. temperatureThe mixture is cooled to room temperature
  5. additionDuring the addition
  6. temperaturethe temperature of the reaction mixture increases to 40° C
  7. stirringThe mixture is then stirred at 60° C
  8. custom(1 hour)
  9. extractionThe oily organic phase is then extracted with 400 ml of 1,2-dichloroethane
  10. washwashed to cyanide-free with 2×200 ml of water
  11. customTraces of 2-(2-thienyl)ethylamine are removed by treatment with 100 ml of 3% hydrochloric acid solution
  12. dry with materialThe dichloroethane phase was dried over anhydrous sodium sulfate
  13. customevaporated in vacuo
  14. customThe residual fast crystallizing oil

Sources & evidence

ORD record
ord-e381fc7c6cc942c0a1ca1e41f549ddee
Source dataset
uspto-grants-2001_07
Patent number
US06258961B1

Reaction notes

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