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

HRID 1888646

반응식

HRID 1888646 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 6212Chloroform용매

반응 조건

온도
60 °C

실험 절차

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)+

후처리

  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)

출처 및 근거

ORD 기록
ord-11c45edbdc4c4ce7b6df836831572b40
출처 데이터셋
uspto-grants-2013_08
특허 번호
US08501794B2

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