Isocyanatocarbonyl chloride → 7-phenyl-6,7-dihydrocyclopenta[e][1,3]oxazine-2,4(3H,5H)-dione

HRID 474252Notes

Reaction equation

HRID 474252 reaction equation
[C:1]1([CH:7]2[CH2:11][CH2:10][CH2:9][C:8]2=[O:12])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:13](Cl)([N:15]=[C:16]=[O:17])=[O:14]>C(OCC)(=O)C.C(=O)(O)[O-].[Na+]>[C:1]1([CH:7]2[C:8]3[O:12][C:16](=[O:17])[NH:15][C:13](=[O:14])[C:9]=3[CH2:10][CH2:11]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 2

HCID 119708Isocyanatocarbonyl chlorideHCID 2901542-Phenylcyclopentanone

Product 1

HCID 105373627-phenyl-6,7-dihydrocyclopenta[e][1,3]oxazine-2,4(3H,5H)-dioneYield 13.1%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 516892Sodium BicarbonateSolvent

Procedure

A solution of 2-phenylcyclopentanone (19.995 g, 125 mmol) and carbonisocyanatidic chloride (23.70 g, 225 mmol) was stirred at 58° C. for 1 h and at 130° C. for 45 min. The resulting tar was dissolved in ethyl acetate and neutralized with saturated aqueous sodium bicarbonate solution. The organic layer was dried over anhydrous magnesium sulfate and filtered. The product was purified by column chromatography on silica gel to give 7-phenyl-6,7-dihydrocyclopenta[e][1,3]oxazine-2,4(3H,5H)-dione (3.751 g, 16.36 mmol, 13% yield) as a brownish solid. LC-MS (M+H)+=230.0. 1H NMR (500 MHz, CDCl3) δ ppm 8.34 (1H, br s), 7.35 (2H, t, J=7.3 Hz), 7.27-7.32 (1H, m), 7.18 (2H, d, J=7.3 Hz), 4.20 (1H, t, J=7.6 Hz), 2.82-2.91 (1H, m), 2.61-2.79 (2H, m), 2.11-2.21 (1H, m).

Workup

  1. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  2. filtrationfiltered
  3. customThe product was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-699f72df7ed549fcbde3232047a02321
Source dataset
uspto-grants-2014_01
Patent number
US08637523B2

Reaction notes

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