Bis(trimethylsilyl)carbodiimide → HCID 178422831, compound

HRID 2096557Notes

Reaction equation

HRID 2096557 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:14](=[CH:15][CH:16]=1)[O:13][C:7]1([CH2:11][CH2:10][CH:9]([CH3:12])[CH2:8]1)[CH2:6][C:5]2=O.C[Si]([N:22]=[C:23]=[N:24][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:14](=[CH:15][CH:16]=1)[O:13][C:7]1([CH2:11][CH2:10][CH:9]([CH3:12])[CH2:8]1)[CH2:6]/[C:5]/2=[N:24]\[C:23]#[N:22]

Participants

5

Reactant 2

HCID 70473Bis(trimethylsilyl)carbodiimideHCID 584244946-Bromo-3'-methylspiro[chroman-2,1'-cyclopentan]-4-one

Product 1

HCID 178422831HCID 178422831, compoundYield 96.6%

Reagents, catalysts & solvents 2

HCID 24193Titanium TetrachlorideCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of 6-bromo-3′-methylspiro[chroman-2,1′-cyclopentan]-4-one (216 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 forl 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 Na2S O4, filtered, and concentrated to give (E)-N-(6-bromo-3′-methylspiro[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. customThe combined organic phases were dried over anhydrous Na2S O4
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-06c7fbab25654ddeae81eb123d424d93
Source dataset
uspto-grants-2013_05
Patent number
US08450308B2

Reaction notes

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