Bis(trimethylsilyl)carbodiimide → HCID 58424074, compound

HRID 2096591Notes

Reaction equation

HRID 2096591 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:17]=[CH:16][CH:15]=[CH:14][N:13]=1)[CH2:6][C:5]2=O.[C:19](=[N:25][Si](C)(C)C)=[N:20][Si](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:17]=[CH:16][CH:15]=[CH:14][N:13]=1)[CH2:6][C:5]2=[N:25][C:19]#[N:20]

Participants

5

Reactant 2

HCID 70473Bis(trimethylsilyl)carbodiimideHCID 10709595HCID 10709595, compound

Product 1

HCID 58424074HCID 58424074, compoundYield 92%

Reagents, catalysts & solvents 2

HCID 24193Titanium TetrachlorideCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of 6-bromo-2-pyridin-2-yl-chroman-4-one (303 mg, 1 mmol) in DCM (10 mL) was added TiCl4 (4 mL, 1 M in CH2Cl2) dropwise within 15 minutes at room temperature. After stirring for 1 h, N,N′-methanediylidenebis(1,1,1-trimethylsilanamine) (0.5 mL, 2.2 mmol) was added dropwise. The mixture was stirred at room temperature overnight and poured into ice-water (50 g). The aqueous layer was extracted with CHCl2, which was combined with the organic layer. The organic layer was dried and concentrated to give crude 6-bromo-2-pyridin-2-yl-chroman-4-ylidene-cyanamide (300 mg, 92%).

Workup

  1. stirringThe mixture was stirred at room temperature overnight
  2. extractionThe aqueous layer was extracted with CHCl2, which
  3. customThe organic layer was dried
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-9cccf581fd3a4c9387a043fffb92e1b1
Source dataset
uspto-grants-2013_05
Patent number
US08450308B2

Reaction notes

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