Bis(trimethylsilyl)carbodiimide → HCID 58424486, compound

HRID 1408829Notes

Reaction equation

HRID 1408829 reaction equation
[C:1]([N:4]1[CH2:9][CH2:8][C:7]2([CH2:18][C:17](=O)[C:16]3[C:11](=[CH:12][CH:13]=[C:14]([C:20]4[CH:21]=[C:22]([CH:25]=[CH:26][CH:27]=4)[C:23]#[N:24])[CH:15]=3)[O:10]2)[CH2:6][CH2:5]1)(=[O:3])[CH3:2].C[Si]([N:32]=[C:33]=[N:34][Si](C)(C)C)(C)C>C(Cl)Cl.Cl[Ti](Cl)(Cl)Cl>[C:1]([N:4]1[CH2:9][CH2:8][C:7]2([CH2:18][C:17](=[N:34][C:33]#[N:32])[C:16]3[C:11](=[CH:12][CH:13]=[C:14]([C:20]4[CH:27]=[CH:26][CH:25]=[C:22]([C:23]#[N:24])[CH:21]=4)[CH:15]=3)[O:10]2)[CH2:6][CH2:5]1)(=[O:3])[CH3:2]

Participants

5

Reactant 2

HCID 70473Bis(trimethylsilyl)carbodiimideHCID 58424199HCID 58424199, compound

Product 1

HCID 58424486HCID 58424486, compound

Reagents, catalysts & solvents 2

HCID 24193Titanium TetrachlorideCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-(1′-acetyl-4-oxospiro[chroman-2,4′-piperidine]-6-yl)benzonitrile (60 mg, 0.167 mmol) in anhydrous DCM (5 mL) under N2 atmosphere was added 1 M TiCl4 (in DCM, 0.35 mL, 0.35 mmol) dropwise within 15 min at room temperature. It was stirred another 1 h after the addition. To this mixture was added Bis-trimethylsilylcarbodiimide (0.086 mL, 0.367 mmol) dropwise. The resulting mixture was stirred overnight. The reaction mixture was quenched with ice-water (5 g), and stirred for 20 min, then it was transferred to a separating funnel, the separated aqueous phase was extracted 2 times with DCM. The combined organic phases were dried over anhydrous Na2SO4, and filtered, and concentrated to give N-(1′-acetyl-6-(3-cyanophenyl)spiro[chroman-2,4′-piperidine]-4-ylidene)cyanamide as light brown solid which was used for next step without further purification. MS ESI+ve m/z 385 (M+H)+.

Workup

  1. additionafter the addition
  2. stirringThe resulting mixture was stirred overnight
  3. customThe reaction mixture was quenched with ice-water (5 g)
  4. stirringstirred for 20 min
  5. customit was transferred to a separating funnel
  6. extractionthe separated aqueous phase was extracted 2 times with DCM
  7. dry with materialThe combined organic phases were dried over anhydrous Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-726d600156264e878046651c8bbb4492
Source dataset
uspto-grants-2014_12
Patent number
US08921359B2

Reaction notes

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