Trimethylsilyl iodide → 2-tert-Butyl-4-butylisothiazol-5(2H)-imine

HRID 1888646

反応式

HRID 1888646 の反応式
[CH2:1]([C:5]1=[CH:6][N:7]([C:16]([CH3:19])([CH3:18])[CH3:17])[S:8]/[C:9]/1=[N:10]\C(=O)OCC)[CH2:2][CH2:3][CH3:4].I[Si](C)(C)C.C(=O)(O)[O-].[Na+]>C(Cl)(Cl)Cl>[C:16]([N:7]1[CH:6]=[C:5]([CH2:1][CH2:2][CH2:3][CH3:4])[C:9](=[NH:10])[S:8]1)([CH3:19])([CH3:18])[CH3:17]

参加物

5

反応物 3

HCID 85247Trimethylsilyl iodideHCID 516892Sodium BicarbonateHCID 87184151ethyl (NZ)-N-(4-butyl-2-tert-butyl-1,2-thiazol-5-ylidene)carbamate

生成物 1

HCID 668672282-tert-Butyl-4-butylisothiazol-5(2H)-imine

試薬・触媒・溶媒 1

HCID 6212Chloroform溶媒

反応条件

温度
60 °C

実験手順

To a 250-mL, round-bottomed flask containing a magnetic stir bar were added the product from Example 92A (7.11 g, 25.0 mmol) and chloroform (100 mL). Neat iodotrimethylsilane (Aldrich, 6.25 g, 31.1 mmol) was added. A reflux condenser with nitrogen inlet was attached and a heating mantle was applied. The yellow reaction mixture was heated to 60° C. and stirred overnight. After cooling to room temperature, saturated aqueous sodium bicarbonate solution was added. The organic layer was separated and the aqueous layer was extracted with dichloromethane (2×50 mL). The combined organic layers were dried (MgSO4), filtered, and concentrated by rotary evaporator to give a yellow semi-solid. The product was purified by flash chromatography (silica get: 30-90% ethyl acetate in hexanes) to afford the title compound. LC-MS (ESI+) m/z 213 (M+H)+

後処理

  1. additionTo a 250-mL, round-bottomed flask containing a magnetic stir bar
  2. customA reflux condenser with nitrogen inlet was attached
  3. temperatureAfter cooling to room temperature
  4. customThe organic layer was separated
  5. extractionthe aqueous layer was extracted with dichloromethane (2×50 mL)
  6. dry with materialThe combined organic layers were dried (MgSO4)
  7. filtrationfiltered
  8. concentrationconcentrated by rotary evaporator
  9. customto give a yellow semi-solid
  10. customThe product was purified by flash chromatography (silica get: 30-90% ethyl acetate in hexanes)

出典と根拠

ORDレコード
ord-11c45edbdc4c4ce7b6df836831572b40
出典データセット
uspto-grants-2013_08
特許番号
US08501794B2

関連ノート

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