Bis(trimethylsilyl)carbodiimide → HCID 178511969, compound

HRID 590530Notes

Reaction equation

HRID 590530 reaction equation
[F:1][C:2]([F:20])([F:19])[C:3]1[CH:4]=[C:5]([C:9]2[S:13][C:12]3[CH2:14][CH2:15][CH2:16][C:17](=O)[C:11]=3[CH:10]=2)[CH:6]=[CH:7][CH:8]=1.C[Si]([N:25]=[C:26]=[N:27][Si](C)(C)C)(C)C>ClCCl.[Ti](Cl)(Cl)(Cl)Cl>[F:1][C:2]([F:20])([F:19])[C:3]1[CH:4]=[C:5]([C:9]2[S:13][C:12]3[CH2:14][CH2:15][CH2:16]/[C:17](=[N:27]\[C:26]#[N:25])/[C:11]=3[CH:10]=2)[CH:6]=[CH:7][CH:8]=1

Participants

5

Reactant 2

HCID 70473Bis(trimethylsilyl)carbodiimideHCID 90070495HCID 90070495, compound

Product 1

HCID 178511969HCID 178511969, compoundYield 99.2%

Reagents, catalysts & solvents 2

HCID 24193Titanium TetrachlorideCatalystHCID 6344DichloromethaneSolvent

Procedure

2-(3-(Trifluoromethyl)phenyl)-6,7-dihydrobenzo[b]thiophen-4(5H)-one (0.252 g, 0.85 mmol) was dissolved in dichloromethane (2 mL). Titanium tetrachloride (1.7 mL, 1.0 M solution in dichloromethane, 1.7 mmol) was added and the reaction mixture was stirred at room temperature for 1 hr. Bis-trimethylsilylcarbodiimide (0.42 mL, 1.87 mmol) was then added and the mixture was stirred at room temperature for 18 hr. The reaction mixture was poured onto ice/water and the product was extracted with dichloromethane. This was back extracted with water and saturated sodium carbonate (aq.) solution. The organic extracts were combined, dried (MgSO4) and concentrated in vacuo to give the title compound as a cream solid (0.27 g, 99%).

Workup

  1. stirringthe mixture was stirred at room temperature for 18 hr
  2. additionThe reaction mixture was poured onto ice/water
  3. extractionthe product was extracted with dichloromethane
  4. extractionThis was back extracted with water and saturated sodium carbonate (aq.) solution
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-6d16612c70854e75875adf8ac79192d9
Source dataset
uspto-grants-2016_01
Patent number
US09233982B2

Reaction notes

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