Chloroform → 4-(1,3-thiazolidin-2-yl)benzonitrile

HRID 250506노트

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HRID 250506 반응식
[C:1]([C:3]1[CH:10]=[CH:9][C:6]([CH:7]=O)=[CH:5][CH:4]=1)#[N:2].Cl.[NH2:12][CH2:13][CH2:14][SH:15].C(Cl)(Cl)Cl>C(O)C.O>[S:15]1[CH2:14][CH2:13][NH:12][CH:7]1[C:6]1[CH:9]=[CH:10][C:3]([C:1]#[N:2])=[CH:4][CH:5]=1

참가 물질

6

반응물 3

HCID 6212ChloroformHCID 9082Cysteamine HydrochlorideHCID 660424-Cyanobenzaldehyde

생성물 1

HCID 113329634-(1,3-thiazolidin-2-yl)benzonitrile수율 67%

시약·촉매·용매 2

HCID 702Ethanol용매HCID 962Water용매

실험 절차

To a solution of 4-cyanobenzaldehyde (0.86 g, 6.6 mmol) in ethanol (15 ml) was added a solution of cysteamine HCl (0.5 g, 4.4 mmol) in water (5 ml) and the solution stirred at RT for 18 h. The bulk of the ethanol was removed by rotary evaporator and the residue was treated with water (15 ml) and extracted with diethyl ether (3×20 ml) to remove excess aldehyde. The aqueous layer was basified with solid sodium carbonate (0.3 g) resulting in the formation of an oil. The mixture was extracted with ether (2×25 ml), washed with brine (1×50 ml), dried (MgSO4) and evaporated to give a clear oil that solidified on standing (0.62 g). Column chromatography (silica gel, 100% chloroform) afforded pure 4-(1,3-thiazolidin-2-yl)benzonitrile (6) (0.56 g, 67%) as clear oil that solidified on standing, mp 57-58°. 1H nmr (CDCl3, 300 MHz) 3.05-3.15, m, H4,4; 3.2-3.35, m, H5; 3.4-3.5, m, H5; 5.64, s, H2; 7.63, app. s, H2′,3′,5′,6′. ESI (+ve) MS m/z 191 (M+H, 100%).

후처리

  1. customThe bulk of the ethanol was removed by rotary evaporator
  2. additionthe residue was treated with water (15 ml)
  3. extractionextracted with diethyl ether (3×20 ml)
  4. customto remove excess aldehyde
  5. customresulting in the formation of an oil
  6. extractionThe mixture was extracted with ether (2×25 ml)
  7. washwashed with brine (1×50 ml)
  8. dry with materialdried (MgSO4)
  9. customevaporated
  10. customto give a clear oil that solidified

출처 및 근거

ORD 기록
ord-0d8215ac021e4a96a4323e26d8bd07a8
출처 데이터셋
uspto-grants-2011_01
특허 번호
US07863313B2

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