Bis(trimethylsilyl)carbodiimide → HCID 178511864, compound

HRID 2096597Notes

Reaction equation

HRID 2096597 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[O:11][C:10]3[CH:12]=[CH:13][CH:14]=[CH:15][C:9]=3[CH2:8][C:7](=O)[C:6]=2[CH:17]=1.C[Si]([N:22]=[C:23]=[N:24][Si](C)(C)C)(C)C>C(Cl)Cl.Cl[Ti](Cl)(Cl)Cl>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[O:11][C:10]3[CH:12]=[CH:13][CH:14]=[CH:15][C:9]=3[CH2:8]/[C:7](=[N:24]\[C:23]#[N:22])/[C:6]=2[CH:17]=1

Participants

5

Reactant 2

HCID 70473Bis(trimethylsilyl)carbodiimideHCID 11651682HCID 11651682, compound

Product 1

HCID 178511864HCID 178511864, compoundYield 68%

Reagents, catalysts & solvents 2

HCID 24193Titanium TetrachlorideCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of 8-chlorodibenzo[b,f]oxepin-10(11H)-one (732 mg, 3.84. mmol) in anhydrous DCM (30 mL) was added TiCl4 (1 M solution in DCM, 7.8 mL, 7.8 mmol) dropwise within 15 minutes at room temperature. It was stirred another 1 h after the addition. To this mixture was added bis-trimethylsilylcarbodiimide (1.48 g, 1.89 mL, 8.46 mmol) dropwise. The resulting mixture was stirred for another 18 h after the addition. The reaction mixture was poured into ice-water (100 g), extracted with DCM (3×50 mL). The combined organic phases were dried over anhydrous Na2SO4, and filtered. The filtrate was concentrated to give (E)-N-(8-chlorodibenzo[b,f]oxepin-10(11H)-ylidene)cyanamide (500 mg, 68%), which was used for 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 (3×50 mL)
  5. dry with materialThe combined organic phases were dried over anhydrous Na2SO4
  6. filtrationfiltered
  7. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-6d45634620624f0785ef8c57711d10f6
Source dataset
uspto-grants-2013_05
Patent number
US08450308B2

Reaction notes

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