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

HRID 250506ノート

反応式

HRID 250506 の反応式
[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

参加物

6

反応物 3

HCID 6212ChloroformHCID 9082Cysteamine HydrochlorideHCID 660424-Cyanobenzaldehyde

生成物 1

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

試薬・触媒・溶媒 2

HCID 702Ethanol溶媒HCID 962Water溶媒

実験手順

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%).

後処理

  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

出典と根拠

ORDレコード
ord-0d8215ac021e4a96a4323e26d8bd07a8
出典データセット
uspto-grants-2011_01
特許番号
US07863313B2

反応ノート

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