Pyridine → HCID 12553762, compound

HRID 1595277Notes

Reaction equation

HRID 1595277 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:10])[CH3:9])=[CH:4][CH:3]=1.N1C=CC=CC=1.Cl[C:18]([O:20][CH2:21][CH:22]([CH3:24])[CH3:23])=[O:19]>C1COCC1.CCOC(C)=O>[C:8]([C:5]1[CH:6]=[CH:7][C:2]([NH:1][C:18](=[O:19])[O:20][CH2:21][CH:22]([CH3:24])[CH3:23])=[CH:3][CH:4]=1)(=[O:10])[CH3:9]

Participants

6

Reactant 3

HCID 1049PyridineHCID 7468p-AminoacetophenoneHCID 62365Isobutyl chloroformate

Product 1

HCID 12553762HCID 12553762, compoundYield 106.7%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a 0° solution of 4′-aminoacetophenone (35 g, 259 mmol) in THF (400 mL) was added pyridine (26 mL, 324 mmol) and isobutyl chloroformate (37 mL, 285 mmol). The resulting heterogeneous mixture was stirred at 0° for 30 min and at room temperature for an additional 30 min. The reaction mixture was then diluted with EtOAc, washed serially with 10% (w/v) aqueous citric acid, 4 N aqueous HCl, H2O, saturated aqueous NaHCO3 and brine, then dried (MgSO4) and concentrated under reduced pressure to yield 2-methylpropyl N-(4-acetylphenyl)carbamate (65 g, quantitative yield) as an off white solid: 1H NMR (400 MHz, CDCl3) δ7.95 (d, 2H, J=8.8 Hz), 7.50 (d, 2H, J=8.8 Hz), 6.85 (s, 1H), 3.99 (d, 2H, J=6.7 Hz), 2.57 (s, 3H), 2.03 (m, 1H), 0.90 (d, 6H, J=6.7 Hz); MS (FAB) m/z 236 (MH)+. This product was used as such in the next reaction (section (b)).

Workup

  1. washwashed serially with 10% (w/v) aqueous citric acid, 4 N aqueous HCl, H2O, saturated aqueous NaHCO3 and brine
  2. dry with materialdried (MgSO4)
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-87a0ea5b08d141f9a81824cca72c42d3
Source dataset
uspto-grants-2001_09
Patent number
US06288091B1

Reaction notes

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