Bis(trimethylsilyl)carbodiimide → HCID 178511907, compound

HRID 2096528Notes

Reaction equation

HRID 2096528 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:25]=[CH:24][CH:23]=[CH:22][N:21]=2)[CH2:3]1.[C:26](=[N:32][Si](C)(C)C)=[N:27][Si](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:25]=[CH:24][CH:23]=[CH:22][N:21]=2)[CH2:3]/[C:2]/3=[N:32]/[C:26]#[N:27])[CH:19]=[CH:18][CH:17]=1)#[N:16]

Participants

5

Reactant 2

HCID 70473Bis(trimethylsilyl)carbodiimideHCID 671744173-(4-Oxo-2-(pyridin-2-yl)chroman-6-yl)benzonitrile

Product 1

HCID 178511907HCID 178511907, compoundYield 190.3%

Reagents, catalysts & solvents 2

HCID 24193Titanium TetrachlorideCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-(4-oxo-2-(pyridin-2-yl)chroman-6-yl)benzonitrile (50 mg, 0.15 mmol) in DCM (2 mL) was added TiCl4 (1 mL, 1 M in CH2Cl2) dropwise within 15 minutes at room temperature. After stirring for 1 h, N,N′-methanediylidenebis(1,1,1-trimethylsilanamine) (0.07 mL, 0.31 mmol) was added dropwise. The mixture was stirred at room temperature overnight and poured into ice-water (25 g). The organic layer was separated and the aqueous layer was extracted with CH2Cl2. The combined organic layer was dried and concentrated to give crude (Z)—N-(6-(3-cyanophenyl)-2-(pyridin-2-yl)chroman-4-ylidene)cyanamide (100 mg, crude).

Workup

  1. stirringThe mixture was stirred at room temperature overnight
  2. customThe organic layer was separated
  3. extractionthe aqueous layer was extracted with CH2Cl2
  4. customThe combined organic layer was dried
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-7afee39b23b94174a8f4ba354ceceb26
Source dataset
uspto-grants-2013_05
Patent number
US08450308B2

Reaction notes

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