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

HRID 323881노트

반응식

HRID 323881 반응식
S(=O)(O)[O-].[Na+].[Cl:6][C:7]1[CH:14]=[CH:13][CH:12]=[CH:11][C:8]=1[CH:9]=O.[S:15]1[CH:19]=[CH:18][CH:17]=[C:16]1[CH2:20][CH2:21][NH2:22].[C-:23]#[N:24].[Na+]>O.C(O)C>[S:15]1[CH:19]=[CH:18][CH:17]=[C:16]1[CH2:20][CH2:21][NH:22][CH:9]([C:8]1[CH:11]=[CH:12][CH:13]=[CH:14][C:7]=1[Cl:6])[C:23]#[N:24]

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 702Ethanol용매HCID 962Water용매2회

반응 조건

온도
40 °C

실험 절차

104 g (1 mol) of sodium bisulfite is dissolved in the mixture of 900 ml of water and 250 ml 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 raises 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 raises 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 elementary analysis, IR spectrum and 1H-NMR investigation.

후처리

  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 the temperature of the reaction mixture
  6. temperatureraises to 40° C
  7. stirringThe mixture is then stirred at 60° C. till the reaction
  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. customare 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

출처 및 근거

ORD 기록
ord-27cb7ad42835487caadb41f0a2b35892
출처 데이터셋
uspto-grants-2001_04
특허 번호
US06215005B1

반응 노트

불러오는 중…