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

HRID 253636

Reaction equation

HRID 253636 reaction equation
[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]

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
60 °C

Procedure

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 gel: 30-90% ethyl acetate in hexanes) to afford the title compound. LC-MS (ESI+) m/z 213 (M+H)+.

Workup

  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 gel: 30-90% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-46403699378d4105b7ad9720346c5bf6
Source dataset
uspto-grants-2011_01
Patent number
US07872033B2

Linked notes

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