Bis(trimethylsilyl)carbodiimide → HCID 178512058, compound

HRID 1408757Notes

Reaction equation

HRID 1408757 reaction equation
CC1(C)[O:7][CH2:6][C:5]2([CH2:16][C:15](=O)[C:14]3[C:9](=[CH:10][CH:11]=[C:12]([C:18]4[CH:19]=[C:20]([CH:23]=[CH:24][CH:25]=4)[C:21]#[N:22])[CH:13]=3)[O:8]2)[CH2:4][O:3]1.C[Si]([N:31]=[C:32]=[N:33][Si](C)(C)C)(C)C>C(Cl)Cl.Cl[Ti](Cl)(Cl)Cl>[C:21]([C:20]1[CH:19]=[C:18]([C:12]2[CH:13]=[C:14]3[C:9](=[CH:10][CH:11]=2)[O:8][C:5]([CH2:6][OH:7])([CH2:4][OH:3])[CH2:16]/[C:15]/3=[N:33]\[C:32]#[N:31])[CH:25]=[CH:24][CH:23]=1)#[N:22]

Participants

5

Reactant 2

HCID 70473Bis(trimethylsilyl)carbodiimideHCID 58424615HCID 58424615, compound

Product 1

HCID 178512058HCID 178512058, compoundYield 109.1%

Reagents, catalysts & solvents 2

HCID 24193Titanium TetrachlorideCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-(2′,2′-dimethyl-4-oxospiro[chroman-2,5′-[1,3]dioxane]-6-yl)benzonitrile (155 mg, 0.44 mmol) in anhydrous DCM (10 mL) under N2 atmosphere was added 1 M TiCl4 (in DCM, 0.88 mL, 0.88 mmol) dropwise within 15 min at room temperature. The mixture was stirred for 1 h after the addition. To this mixture was added bis-trimethylsilylcarbodiimide (181 mg, 217 μL 0.97 mmol) dropwise. The resulting mixture was stirred for another 20 h after the addition. The reaction mixture was poured into ice-water (25 g), stirred for 30 min and filtered through a pad of Celite. The separated aqueous phase of the filtrate was extracted with DCM once. The combined organic phases were dried over anhydrous Na2SO4, filtered, and concentrated to give yellowish gel like solid (E)-N-(6-(3-cyanophenyl)-2,2-bis(hydroxymethyl)chroman-4-ylidene)cyanamide (160 mg), which was used in the next step without further purification. MS ESI+ve m/z 374 (M+H)+.

Workup

  1. additionafter the addition
  2. stirringThe resulting mixture was stirred for another 20 h
  3. additionafter the addition
  4. stirringstirred for 30 min
  5. filtrationfiltered through a pad of Celite
  6. extractionThe separated aqueous phase of the filtrate was extracted with DCM once
  7. dry with materialThe combined organic phases were dried over anhydrous Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-567cd8fda613434495f489b756afdaab
Source dataset
uspto-grants-2014_12
Patent number
US08921359B2

Reaction notes

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