Acetone → HCID 68292872, compound

HRID 1504951Notes

Reaction equation

HRID 1504951 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]([NH2:19])=[O:18])=[CH:10][CH:9]=1.[CH3:20][C:21]([CH3:23])=O>>[C:5]([C:21]([NH:7][C:8]1[CH:9]=[CH:10][C:11]([CH2:14][CH2:15][CH2:16][C:17]([NH2:19])=[O:18])=[CH:12][CH:13]=1)([CH3:23])[CH3:20])#[N:6]

Participants

4

Reactant 3

HCID 180AcetoneHCID 82115Trimethylsilyl cyanideHCID 54549569HCID 54549569, compound

Product 1

HCID 68292872HCID 68292872, compoundYield 41.3%

Conditions

Temperature
40 °C

Procedure

TMSCN (0.3 mL, 2.36 mmol) was added to a mixture of the compound 33 (140 mg, 0.79 mmol), acetone (0.35 mL, 1.56 mmol) and 12 (10 mg, 0.08 mmol). The reaction mixture was stirred at 40° C. for 1 h. The reaction was concentrated in vacuo. The residue was diluted with aqNa2SO3, and extracted with ethyl acetate. The combined organic layers were washed with aqNa2SO3 and brine, dried over Na2SO4 and concentrated to dryness to give compound 34 (80 mg) 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=8.5 Hz), 6.88 (d, 2H, J=8.5 Hz), 5.29 (br s, 1H), 2.61 (t, 2H, J=7.4 Hz), 2.20 (t, 2H, J=7.4 Hz), 1.87-1.97 (m, 2H), 1.68 (s, 6H).

Workup

  1. concentrationThe reaction was concentrated in vacuo
  2. additionThe residue was diluted with aqNa2SO3
  3. extractionextracted with ethyl acetate
  4. washThe combined organic layers were washed with aqNa2SO3 and brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-9e0dda07c3d2414f93d45261fc9b98f0
Source dataset
uspto-grants-2015_12
Patent number
US09216957B2

Reaction notes

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