Sodium Cyanide → 1-(Diphenylmethyl)azetidine-3-carbonitrile

HRID 865026노트

반응식

HRID 865026 반응식
[CH:1]([N:14]1[CH2:17][CH:16](OS(C)(=O)=O)[CH2:15]1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C-:23]#[N:24].[Na+]>CN(C)C=O.O>[CH:1]([N:14]1[CH2:17][CH:16]([C:23]#[N:24])[CH2:15]1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

참가 물질

5

반응물 2

HCID 8929Sodium CyanideHCID 27587161-(Diphenylmethyl)azetidin-3-yl methanesulfonate

생성물 1

HCID 27792901-(Diphenylmethyl)azetidine-3-carbonitrile수율 51.3%

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매

반응 조건

온도
60 °C

실험 절차

A mixture of 50 g (0.157 mol) of 1-benzhydryl-3-mesyloxyazetidine (J. Org. Chem. 1972, 37, 3953-3955) and 23.5 g (0.479 mol) of sodium cyanide in 340 ml of dimethylformamide and 43 ml of water is heated to 60° C. for 5 hours. The reaction mixture is left at ambient temperature overnight and is then poured into 2000 ml of water/ice. The solid product is recovered by filtration and is purified by being suspended in 800 ml of water and being filtered. The product thus obtained is dried and crystallized from isopropyl ether to obtain 20 g of 1-benzhydryl-3-azetidinecarbonitrile. M.p. 142°-146° C.

후처리

  1. filtrationThe solid product is recovered by filtration
  2. customis purified
  3. filtrationbeing filtered
  4. customThe product thus obtained
  5. customis dried
  6. customcrystallized from isopropyl ether

출처 및 근거

ORD 기록
ord-2993db46b6ac4e8e91a517121cc8ed03
출처 데이터셋
uspto-grants-1996_10
특허 번호
US05565474

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