2-Bromothiophene → HCID 20041072, 화합물

HRID 1762462노트

반응식

HRID 1762462 반응식
BrC1SC=CC=1.[Mg].[Cl:8][C:9]1[CH:10]=[C:11]([C:16]2(C#N)[CH2:19][CH2:18][CH2:17]2)[CH:12]=[CH:13][C:14]=1[Cl:15].[S:22]1[CH:26]=[CH:25][CH:24]=[C:23]1[CH:27]=[N:28][Mg]Br>CCOCC>[ClH:8].[Cl:8][C:9]1[CH:10]=[C:11]([C:16]2([NH:28][CH2:27][C:23]3[S:22][CH:26]=[CH:25][CH:24]=3)[CH2:17][CH2:18][CH2:19]2)[CH:12]=[CH:13][C:14]=1[Cl:15]

참가 물질

6

반응물 4

HCID 138512-BromothiopheneHCID 5462224Magnesium2회HCID 108571341-(3,4-Dichlorophenyl)-1-cyclobutane-carbonitrileHCID 178419685HCID 178419685, 화합물

생성물 1

HCID 20041072HCID 20041072, 화합물

시약·촉매·용매 1

HCID 3283Diethyl Ether용매3회

반응 조건

온도
20 °C

실험 절차

A solution of 2-bromothiophene (32.9 g) in dry ether (50 ml) was added dropwise to a stirred mixture of magnesium turnings (4.85 g) and ether (50 ml) under nitrogen. When all the magnesium had dissolved a solution of 1-(3,4-dichlorophenyl)cyclobutanecarbonitrile (30.6 g) in dry ether (200 ml) was added and the mixture stirred at 20° C. for one hour and then heated under reflux for one hour. A solid formed which is believed to be 1-(3,4-dichlorophenyl)cyclobutyl](thien-2-yl)methaniminylmagnesium bromide and was collected by filtration. The solid was dissolved in ethanol (200 ml) and a solution of sodium borohydride (10 g) in ethanol (500 ml) added and the mixture heated under reflux for four hours. The mixture was cooled and water (200 ml) and then 5N hydrochloric acid added. The ethanol was removed by evaporation and the aqueous solution basified by the addition of 5N sodium hydroxide solution. The aqueous layer was extracted with ether and the extract dried. Hydrogen chloride gas was passed into the ethereal solution to give [1-(3,4-dichlorophenyl)cyclobutyl](thien-2-yl)methylamine hydrochloride (m.p. 238°-242° C.).

후처리

  1. additionwas added
  2. temperatureheated
  3. temperatureunder reflux for one hour
  4. customA solid formed which
  5. filtrationwas collected by filtration
  6. dissolutionThe solid was dissolved in ethanol (200 ml)
  7. additiona solution of sodium borohydride (10 g) in ethanol (500 ml) added
  8. temperaturethe mixture heated
  9. temperatureunder reflux for four hours
  10. temperatureThe mixture was cooled
  11. additionwater (200 ml) and then 5N hydrochloric acid added
  12. customThe ethanol was removed by evaporation
  13. additionthe aqueous solution basified by the addition of 5N sodium hydroxide solution
  14. extractionThe aqueous layer was extracted with ether
  15. customthe extract dried

출처 및 근거

ORD 기록
ord-98befdcbbc8b4d168956f5357f7f1f7d
출처 데이터셋
uspto-grants-1989_05
특허 번호
US04833143

반응 노트

불러오는 중…