Bis(trimethylsilyl)carbodiimide → HCID 178511916, compound

HRID 2096593Notes

Reaction equation

HRID 2096593 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[O:8][CH:7]([C:12]1[CH:13]=[N:14][CH:15]=[CH:16][CH:17]=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:9](=[CH:10][CH:11]=1)[O:8][CH:7]([C:12]1[CH:13]=[N:14][CH:15]=[CH:16][CH:17]=1)[CH2:6]/[C:5]/2=[N:25]\[C:24]#[N:23]

Participants

5

Reactant 2

HCID 70473Bis(trimethylsilyl)carbodiimideHCID 10780793HCID 10780793, compound

Product 1

HCID 178511916HCID 178511916, compoundYield 64%

Reagents, catalysts & solvents 2

HCID 24193Titanium TetrachlorideCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of 6-bromo-2-(pyridine-3-yl)chroman-4-one (1.0 g, 3.3 mmol) in anhydrous DCM (20 mL) was added TiCl4 (1 M solution in DCM, 2.5 g, 13.2 mmol) dropwise within 15 minutes at room temperature in absence of light. It was stirred for another 1 h after the addition. To this mixture was added bis-trimethylsilylcarbodiimide (1.35 g, 7.26 mmol) dropwise. The resulting mixture was stirred overnight. The reaction mixture was poured into ice-water, extracted with DCM. The combined organic phases were dried over anhydrous Na2SO4, and filtered. The filtrate was concentrated to give (E)-N-(6-bromo-2-(pyridine-3-yl)chroman-4-ylidene)cyanamide (687 mg, 64%), which was used for next step without further purification.

Workup

  1. additionafter the addition
  2. stirringThe resulting mixture was stirred overnight
  3. extractionextracted with DCM
  4. dry with materialThe combined organic phases were dried over anhydrous Na2SO4
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-8f9cc81357894ec4a3ff1c9671d97c07
Source dataset
uspto-grants-2013_05
Patent number
US08450308B2

Reaction notes

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