Acetone → HCID 68292334, compound

HRID 1504947Notes

Reaction equation

HRID 1504947 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]([O:19][CH3:20])=[O:18])=[CH:10][CH:9]=1.[CH3:21][C:22]([CH3:24])=O>>[C:5]([C:22]([NH:7][C:8]1[CH:9]=[CH:10][C:11]([CH2:14][CH2:15][CH2:16][C:17]([O:19][CH3:20])=[O:18])=[CH:12][CH:13]=1)([CH3:24])[CH3:21])#[N:6]

Participants

4

Reactant 3

HCID 180AcetoneHCID 82115Trimethylsilyl cyanideHCID 88628Methyl 4-aminobenzenebutanoate

Product 1

HCID 68292334HCID 68292334, compoundYield 96%

Procedure

TMSCN (1.44 mL, 10.8 mmol) was added to a mixture of the compound 27 (0.7 g, 3.6 mmol), acetone (1.60 mL, 21.6 mmol) and 12 (50 mg, 0.4 mmol) with stirring. The reaction mixture was stirred at 50° C. for 0.5 h. The reaction was concentrated in vacuo. The residue was diluted with aq Na2SO3 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 28 (0.9 g) as a light yellow oil. The crude product was used directly for the next step without purification. 1H NMR (400 MHz, CDCl3) δ7.07 (d, 2H, J=8.3 Hz), 6.87 (d, 2H, J=8.3 Hz), 3.66 (s, 3H), 2.58 (t, 2H, J=7.4 Hz), 2.32 (t, 2H, J=7.4 Hz), 1.85-1.95 (m, 2H), 1.68 (s, 6H).

Workup

  1. stirringThe reaction mixture was stirred at 50° C. for 0.5 h
  2. concentrationThe reaction was concentrated in vacuo
  3. additionThe residue was diluted with aq Na2SO3
  4. extractionextracted with ethyl acetate
  5. washThe combined organic layers were washed with aqNa2SO3 and brine
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-20dfcbe034b04f1a8391ff926d8ff11a
Source dataset
uspto-grants-2015_12
Patent number
US09216957B2

Reaction notes

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