Bis(trimethylsilyl)carbodiimide → HCID 178423821, compound

HRID 1408799Notes

Reaction equation

HRID 1408799 reaction equation
[CH3:1][C:2]1([CH3:27])[CH2:7][CH:6]([CH:8]2[CH2:17][C:16](=O)[C:15]3[C:10](=[CH:11][CH:12]=[C:13]([C:19]4[CH:20]=[C:21]([CH:24]=[CH:25][CH:26]=4)[C:22]#[N:23])[CH:14]=3)[O:9]2)[CH2:5][CH2:4][O:3]1.C[Si]([N:32]=[C:33]=[N:34][Si](C)(C)C)(C)C>C(Cl)Cl.Cl[Ti](Cl)(Cl)Cl>[C:22]([C:21]1[CH:20]=[C:19]([C:13]2[CH:14]=[C:15]3[C:10](=[CH:11][CH:12]=2)[O:9][CH:8]([CH:6]2[CH2:5][CH2:4][O:3][C:2]([CH3:27])([CH3:1])[CH2:7]2)[CH2:17]/[C:16]/3=[N:34]\[C:33]#[N:32])[CH:26]=[CH:25][CH:24]=1)#[N:23]

Participants

5

Reactant 2

HCID 70473Bis(trimethylsilyl)carbodiimideHCID 671748323-(2-(2,2-dimethyltetrahydro-2H-pyran-4-yl)-4-oxochroman-6-yl)benzonitrile

Product 1

HCID 178423821HCID 178423821, compoundYield 103.8%

Reagents, catalysts & solvents 2

HCID 24193Titanium TetrachlorideCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-(2-(2,2-dimethyltetrahydro-2H-pyran-4-yl)-4-oxochroman-6-yl)benzonitrile (251 mg, 0.69 mmol) in anhydrous DCM (15 mL) under N2 atmosphere was added 1 M TiCl4 (in DCM, 1.4 mL, 1.4 mmol) dropwise within 5 min at room temperature. It was stirred another 1 h after the addition. To this mixture was added Bis-trimethylsilylcarbodiimide (283 mg, 340 μL 1.52 mmol) dropwise. The resulting mixture was stirred for another 20 h after the addition. The reaction mixture was poured into ice-water (20 g), It was transferred to a separating funnel after stirred for 30. The separated aqueous phase was extracted with DCM (2×20 mL). The combined organic phases were dried over anhydrous Na2SO4, and filtered, and concentrated to give yellowish gel like solid (E)-N-(6-(3-cyanophenyl)-2-(2,2-dimethyltetrahydro-2H-pyran-4-yl)chroman-4-ylidene)cyanamide (276 mg), which was used for next step without further purification. MS ESI+ve m/z 386 (M+H)+.

Workup

  1. additionafter the addition
  2. stirringThe resulting mixture was stirred for another 20 h
  3. additionafter the addition
  4. customwas transferred to a separating funnel
  5. stirringafter stirred for 30
  6. extractionThe separated aqueous phase was extracted with DCM (2×20 mL)
  7. dry with materialThe combined organic phases were dried over anhydrous Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-dc552f5b07fa471e80a1d24f0a6b8553
Source dataset
uspto-grants-2014_12
Patent number
US08921359B2

Reaction notes

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