Bis(trimethylsilyl)carbodiimide → HCID 178435536, compound

HRID 2096550Notes

Reaction equation

HRID 2096550 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:15](=[CH:16][CH:17]=1)[O:14][C:7]1([CH2:11][CH2:10][CH:9]([CH2:12][CH3:13])[CH2:8]1)[CH2:6][C:5]2=O.C[Si]([N:23]=[C:24]=[N:25][Si](C)(C)C)(C)C>C(Cl)Cl.Cl[Ti](Cl)(Cl)Cl>[Br:1][C:2]1[CH:3]=[C:4]2[C:15](=[CH:16][CH:17]=1)[O:14][C:7]1([CH2:11][CH2:10][CH:9]([CH2:12][CH3:13])[CH2:8]1)[CH2:6]/[C:5]/2=[N:25]\[C:24]#[N:23]

Participants

5

Reactant 2

HCID 70473Bis(trimethylsilyl)carbodiimideHCID 58424743HCID 58424743, compound

Product 1

HCID 178435536HCID 178435536, compoundYield 92.5%

Reagents, catalysts & solvents 2

HCID 24193Titanium TetrachlorideCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of 6-bromo-3′-ethylspiro[chroman-2,1′-cyclopentan]-4-one (226 mg, 0.73 mmol) in anhydrous DCM (5.7 mL) was added TiCl4 (1 M solution in DCM, 1.5 mL, 1.49 mmol) dropwise within 15 min at room temperature. The mixture was stirred another 1 h after the addition. To this mixture was added Bis-trimethylsilylcarbodiimide (300 mg, 0.36 mL, 1.61 mmol) dropwise. The resulting mixture was stirred for another 18 h after the addition. The reaction mixture was poured into ice-water (20 g) and extracted with DCM (3×20 mL). The combined organic phases were dried over anhydrous Na2SO4, filtered, and concentrated to give (E)-N-(6-bromo-3′-ethylspiro[chroman-2,1′-cyclopentane]-4-ylidene)cyanamide as light brown solid (225 mg), which was used in the next step without further purification.

Workup

  1. additionafter the addition
  2. stirringThe resulting mixture was stirred for another 18 h
  3. additionafter the addition
  4. extractionextracted with DCM (3×20 mL)
  5. dry with materialThe combined organic phases were dried over anhydrous Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-244dab5ff8a149a58d62ea11eb3d87bb
Source dataset
uspto-grants-2013_05
Patent number
US08450308B2

Reaction notes

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