Bis(trimethylsilyl)carbodiimide → HCID 178511905, compound

HRID 2096536Notes

Reaction equation

HRID 2096536 reaction equation
[O:1]([C:8]1[CH:9]=[C:10]2[C:15](=[CH:16][CH:17]=1)[O:14][CH:13]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[CH2:12][C:11]2=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C[Si]([N:29]=[C:30]=[N:31][Si](C)(C)C)(C)C>C(Cl)Cl.Cl[Ti](Cl)(Cl)Cl>[O:1]([C:8]1[CH:9]=[C:10]2[C:15](=[CH:16][CH:17]=1)[O:14][CH:13]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[CH2:12]/[C:11]/2=[N:31]/[C:30]#[N:29])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 70473Bis(trimethylsilyl)carbodiimideHCID 58424102HCID 58424102, compound

Product 1

HCID 178511905HCID 178511905, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 24193Titanium TetrachlorideCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of 6-phenoxy-2-phenylchroman-4-one (316 mg, 1. mmol) in anhydrous DCM (7.8 mL) was added TiCl4 (1 M solution in DCM, 2 mL, 2 mmol) dropwise within 15 minutes at room temperature. After addition, the mixture was stirred for 1 h. To this mixture was added bis-trimethylsilylcarbodiimide (0.41 g, 0.49 mL, 2.2 mmol) dropwise. The resulting mixture was stirred for another 18 h after the addition. The reaction mixture was poured into ice-water (50 g) and extracted with DCM (3×30 mL). The combined organic phases were dried over anhydrous Na2SO4, and filtered. The filtrate was concentrated to give (Z)—N-(6-phenoxy-2-phenylchroman-4-ylidene)cyanamide (340 mg, 90%), which was used in the next step without further purification.

Workup

  1. additionAfter addition
  2. stirringThe resulting mixture was stirred for another 18 h
  3. additionafter the addition
  4. extractionextracted with DCM (3×30 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-e0d7e8aea0e747e7a07a511b4d5ae60e
Source dataset
uspto-grants-2013_05
Patent number
US08450308B2

Reaction notes

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