Tetrahydrofuran → 2-(tert-Butyldimethylsilyl)-N,N-dimethyl-1H-imidazole-1-sulfonamide

HRID 28727

反応式

HRID 28727 の反応式
[CH3:1][N:2]([CH3:11])[S:3]([N:6]1[CH:10]=[CH:9][N:8]=[CH:7]1)(=[O:5])=[O:4].C1COCC1.[Li]CCCC.[Si:22](Cl)([C:25]([CH3:28])([CH3:27])[CH3:26])([CH3:24])[CH3:23]>O>[CH3:1][N:2]([CH3:11])[S:3]([N:6]1[CH:10]=[CH:9][N:8]=[C:7]1[Si:22]([C:25]([CH3:28])([CH3:27])[CH3:26])([CH3:24])[CH3:23])(=[O:4])=[O:5]

参加物

6

反応物 4

HCID 8028TetrahydrofuranHCID 28928tert-Butyldimethylsilyl chlorideHCID 395751N,N-Dimethyl-1H-imidazole-1-sulfonamideHCID 178418339Butyllithium

生成物 1

HCID 64202092-(tert-Butyldimethylsilyl)-N,N-dimethyl-1H-imidazole-1-sulfonamide

試薬・触媒・溶媒 1

HCID 962Water溶媒

反応条件

温度
-78 °C

実験手順

Imidazole (Intermediate L1, available from Aldrich, 20.0 g, 0.29 mol), triethylamine (41.0 mL, 0.29 mol) and N,N-dimethylsulfamoyl chloride (31.6 mL, 0.29 mol) were added to benzene (320 mL). The reaction was stirred for 48 h at rt and then filtered. The filtrate was collected and concentrated under reduced pressure. Vacuum distillation of the crude produc (˜0.5 mmHg, 115-118° C.) afforded dimethylsulfamoyl)imidazole (Intermediate L2) 38.7 g (76%) as a clear and colorless oil. Upon cooling the product solidifies to give white crystals. 1-(Dimethylsulfamoyl)imidazole (Intermediate L2) (18.8 g, 0.11 mol) was added to THF (430 mL). The solution was cooled to −78° C. A solution of n-BuLi (70.9 mL, 1.6 M in hexane) was added dropwise to the reaction mixture. Upon completion, the solution was stirred for 1 h at −78° C. t-Butyldimethylsilylchloride (TBSCl) (17.8 g, 0.12 mol) in THE (50 mL) was added via cannula to the mixture. After the addition was completed the reaction mixture was warmed slowly to rt and stirred for 24 h. The mixture was diluted with water and the organic layer separated. The organic phase was washed with brine and then dried over Na2SO4. The mixture was filtered and the filtrate concentrated under reduced pressure. Column chromatography on SiO2 with 20% ethyl acetate/hexane afforded 1-dimethylsulfamoyl-2-t-butyldimethylsilyl imidazole (Formula 13) as a light yellow solid. Recrystallization from pentane gave 30 g (94%) of white crystals.

後処理

  1. temperatureUpon cooling the product
  2. customto give white crystals
  3. additionwas added via cannula to the mixture
  4. additionAfter the addition
  5. temperaturewas warmed slowly to rt
  6. customthe organic layer separated
  7. washThe organic phase was washed with brine
  8. dry with materialdried over Na2SO4
  9. filtrationThe mixture was filtered
  10. concentrationthe filtrate concentrated under reduced pressure

出典と根拠

ORDレコード
ord-ad3fd7793e5b448f9e14b5d63fe9a2bf
出典データセット
uspto-grants-2008_09
特許番号
US07419994B2

関連ノート

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