Bis(trimethylsilyl)carbodiimide → HCID 178511869, compound

HRID 1408735Notes

Reaction equation

HRID 1408735 reaction equation
O=[C:2]1[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([C:17]3[CH:18]=[C:19]([CH:22]=[CH:23][CH:24]=3)[C:20]#[N:21])[CH:15]=2)[O:10][C:4]2([CH2:9][CH2:8][O:7][CH2:6][CH2:5]2)[CH2:3]1.C[Si]([N:29]=[C:30]=[N:31][Si](C)(C)C)(C)C>C(Cl)Cl.Cl[Ti](Cl)(Cl)Cl>[C:20]([C:19]1[CH:18]=[C:17]([C:14]2[CH:15]=[C:16]3[C:11](=[CH:12][CH:13]=2)[O:10][C:4]2([CH2:5][CH2:6][O:7][CH2:8][CH2:9]2)[CH2:3]/[C:2]/3=[N:29]/[C:30]#[N:31])[CH:24]=[CH:23][CH:22]=1)#[N:21]

Participants

5

Reactant 2

HCID 70473Bis(trimethylsilyl)carbodiimideHCID 67174251HCID 67174251, compound

Product 1

HCID 178511869HCID 178511869, compoundYield 80.8%

Reagents, catalysts & solvents 2

HCID 24193Titanium TetrachlorideCatalystHCID 6344DichloromethaneSolvent

Procedure

A solution of 3-(4-oxo-2′,3′,5′,6′-tetrahydrospiro[chroman-2,4′-pyran]-6-yl)benzonitrile (170 mg, 0.53 mmol) and TiCl4 (403 mg, 2.12 mmol) in anhydrous DCM (5 mL) was heated at 50 under microwave for 5 mins. Then bis-trimethylsilylcarbodiimide (198 mg, 1.06 mmol) was added and the mixture was heated at 60 for another 30 mins. The reaction mixture was poured into ice-water and extracted with DCM. The combined organic phases were dried over anhydrous Na2SO4, filtered and concentrated to give (Z)—N-(6-(3-cyanophenyl)-2′,3′,5′,6′-tetrahydrospiro[chroman-2,4′-pyran]-4-ylidene)cyanamide (147 mg, crude), which was used in the next step without further purification.

Workup

  1. temperaturethe mixture was heated at 60 for another 30 mins
  2. extractionextracted with DCM
  3. dry with materialThe combined organic phases were dried over anhydrous Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-ee2a38753b134d53b5fce685e15ca3fa
Source dataset
uspto-grants-2014_12
Patent number
US08921359B2

Reaction notes

Loading…