Bis(trimethylsilyl)carbodiimide → HCID 58424747, compound

HRID 2096636Notes

Reaction equation

HRID 2096636 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]([CH2:20][CH:21]2[CH2:25][CH2:24][CH2:23][O:22]2)[CH2:3]1.C[Si]([N:30]=[C:31]=[N:32][Si](C)(C)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]([CH2:20][CH:21]2[CH2:25][CH2:24][CH2:23][O:22]2)[CH2:3][C:2]3=[N:32][C:31]#[N:30])[CH:19]=[CH:18][CH:17]=1)#[N:16]

Participants

5

Reactant 2

HCID 70473Bis(trimethylsilyl)carbodiimideHCID 58424394HCID 58424394, compound

Product 1

HCID 58424747HCID 58424747, compound

Reagents, catalysts & solvents 2

HCID 24193Titanium TetrachlorideCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-(4-oxo-2-((tetrahydrofuran-2-yl)methyl)chroman-6-yl)benzonitrile (233 mg, 0.70 mmol) in anhydrous DCM (18 mL) under N2 atmosphere was added 1 M TiCl4 (in DCM, 1.4 mL, 1.4 mmol) dropwise within 15 min at room temperature. It was stirred another 1 h after the addition. To this mixture was added Bis-trimethylsilylcarbodiimide (0.287 g, 0.35 mL, 1.54 mmol) dropwise. The resulting mixture was stirred overnight after the addition. The reaction mixture was poured into ice-water (25 g), and stirred for 30 min, then it was transferred to a separating funnel, the separated aqueous phase was extracted twice with DCM (2×30 mL). The combined organic phases were dried over anhydrous Na2SO4, and filtered, and concentrated to give N-(6-(3-cyanophenyl)-2-((tetrahydrofuran-2-yl)methyl)chroman-4-ylidene)cyanamide as light brown solid, which was used for next step without further purification. MS ESI +ve m/z 358 (M+H)+.

Workup

  1. additionafter the addition
  2. stirringThe resulting mixture was stirred overnight
  3. additionafter the addition
  4. stirringstirred for 30 min
  5. customit was transferred to a separating funnel
  6. extractionthe separated aqueous phase was extracted twice with DCM (2×30 mL)
  7. dry with materialThe combined organic phases were dried over anhydrous Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-07512de895fa4cb7b6c7386187cb63ae
Source dataset
uspto-grants-2013_05
Patent number
US08450308B2

Reaction notes

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