Bis(trimethylsilyl)carbodiimide → HCID 178511917, compound

HRID 2096511Notes

Reaction equation

HRID 2096511 reaction equation
O=[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([C:12]3[CH:13]=[C:14]([CH:17]=[CH:18][CH:19]=3)[C:15]#[N:16])[CH:10]=2)[O:5][CH:4]([C:20]2[CH:21]=[N:22][CH:23]=[CH:24][CH:25]=2)[CH2:3]1.C[Si]([N:30]=[C:31]=[N:32][Si](C)(C)C)(C)C>C(Cl)Cl.Cl[Ti](Cl)(Cl)Cl>[C:15]([C:14]1[CH:13]=[C:12]([C:9]2[CH:10]=[C:11]3[C:6](=[CH:7][CH:8]=2)[O:5][CH:4]([C:20]2[CH:21]=[N:22][CH:23]=[CH:24][CH:25]=2)[CH2:3]/[C:2]/3=[N:32]\[C:31]#[N:30])[CH:19]=[CH:18][CH:17]=1)#[N:16]

Participants

5

Reactant 2

HCID 70473Bis(trimethylsilyl)carbodiimideHCID 67174135HCID 67174135, compound

Product 1

HCID 178511917HCID 178511917, compoundYield 93%

Reagents, catalysts & solvents 2

HCID 24193Titanium TetrachlorideCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-(4-oxo-2-(pyridine-3-yl)chroman-6-yl)benzonitrile (70 mg, 0.22 mmol) in anhydrous DCM (3 mL) was added TiCl4 (1 M solution in DCM, 293 mg, 1.54 mmol) dropwise within 15 minutes at room temperature in the absence of light. The resulting mixture was stirred for 1 h after the addition. To this mixture was added bis-trimethylsilylcarbodiimide (164 mg, 0.88 mmol) dropwise. The resulting mixture was stirred overnight. The reaction mixture was poured into ice-water and extracted with DCM. The combined organic phases were dried over anhydrous Na2SO4, and filtered. The filtrate was concentrated to give (E)-N-(6-(3-cyanophenyl)-2-(pyridine-3-yl)chroman-4-ylidene)cyanamide (70 mg, 93%), which was used in 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-9c32173950e5426cb97d5fde50fad54c
Source dataset
uspto-grants-2013_05
Patent number
US08450308B2

Reaction notes

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