Acetone → HCID 44603856, compound

HRID 1504969Notes

Reaction equation

HRID 1504969 reaction equation
[Si]([C:5]#[N:6])(C)(C)C.[NH2:7][C:8]1[CH:13]=[CH:12][C:11]([CH2:14][CH2:15][CH2:16][C:17]#[N:18])=[CH:10][CH:9]=1.[CH3:19][C:20]([CH3:22])=O>[Cl-].[Cl-].[Zn+2]>[C:5]([C:20]([NH:7][C:8]1[CH:9]=[CH:10][C:11]([CH2:14][CH2:15][CH2:16][C:17]#[N:18])=[CH:12][CH:13]=1)([CH3:22])[CH3:19])#[N:6]

Participants

5

Reactant 3

HCID 180AcetoneHCID 82115Trimethylsilyl cyanideHCID 12547487HCID 12547487, compound

Product 1

HCID 44603856HCID 44603856, compoundYield 99.7%

Reagents, catalysts & solvents 1

HCID 3007855ZincchlorideCatalyst

Procedure

TMSCN (0.3 mL, 2.25 mmol) was added to a mixture of compound 83 (120 mg, 0.75 mmol), acetone (0.33 mL, 4.5 mmol) and ZnCl2 (10 mg, 0.08 mmol) with stirring. The reaction mixture was stirred at room temperature for 1 h, and concentrated in vacuo. The residue was diluted with water, and extracted with DCM. The combined organic layers were washed with brine, dried over Na2SO4 and concentrated to dryness to give compound 84 (170 mg, 99%) as a light yellow oil. The crude product was used directly for the next step without purification. 1H NMR (400 MHz, CDCl3) δ7.08 (d, 2H, J=8.1 Hz), 6.88 (d, 2H, J=8.1 Hz), 2.72 (t, 2H, J=7.4 Hz), 2.32 (t, 2H, J=7.4 Hz), 1.90-2.00 (m, 2H), 1.69 (s, 6H).

Workup

  1. stirringThe reaction mixture was stirred at room temperature for 1 h
  2. concentrationconcentrated in vacuo
  3. additionThe residue was diluted with water
  4. extractionextracted with DCM
  5. washThe combined organic layers were washed with brine
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-722c3f4dddc647888a5e5dc9ee542ff3
Source dataset
uspto-grants-2015_12
Patent number
US09216957B2

Reaction notes

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