Bis(trimethylsilyl)carbodiimide → HCID 178511869, compound

HRID 2096547Notes

Reaction equation

HRID 2096547 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

Conditions

Temperature
60 °C

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° C. under microwave for 5 mins. Then bis-trimethylsilylcarbodiimide (198 mg, 1.06 mmol) was added and the mixture was heated at 60° C. 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. extractionextracted with DCM
  2. dry with materialThe combined organic phases were dried over anhydrous Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-e99fdcd9a22b4eb88b7a87f207b6a089
Source dataset
uspto-grants-2013_05
Patent number
US08450308B2

Reaction notes

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