Isocyanatocarbonyl chloride → HCID 58075569, compound

HRID 475748Notes

Reaction equation

HRID 475748 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[CH2:12][CH2:11][CH2:10][C:9]2=[O:13])=[CH:4][CH:3]=1.[C:14](Cl)([N:16]=[C:17]=[O:18])=[O:15]>C(OCC)(=O)C>[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]2[C:9]3[O:13][C:17](=[O:18])[NH:16][C:14](=[O:15])[C:10]=3[CH2:11][CH2:12]2)=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 119708Isocyanatocarbonyl chlorideHCID 24787891HCID 24787891, compound

Product 1

HCID 58075569HCID 58075569, compoundYield 52.6%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
130 °C

Procedure

A mixture of 2-(4-fluorophenyl)cyclopentanone (18.557 g, 104 mmol) and carbonisocyanatidic chloride (19.77 g, 187 mmol) was heated at 58° C. for 1 h and at 130° C. for 2 h. Upon cooling to room temperature, the tarrified reaction mixture was dissolved in ethyl acetate and washed with saturated aqueous solution of sodium bicarbonate. The organic layer was separated and the aqueous layer was extracted with ethyl acetate. The combined organic extracts were dried over anhydrous magnesium sulfate and filtered. The solvent was removed in vacuum and the residue was purified by column chromatography on silica gel to give 7-(4-fluorophenyl)-6,7-dihydrocyclopenta[e][1,3]oxazine-2,4(3H,5H)-dione (13.527 g, 54.7 mmol, 52.5% yield) as brown solid. LC-MS (M+H)+=248.1. 1H NMR (500 MHz, CDCl3) δ ppm 11.80 (1H, br s), 7.31-7.39 (2H, m), 7.16-7.22 (2H, m), 4.30-4.38 (1H, m), 2.63-2.73 (1H, m), 2.53-2.63 (2H, m), 1.84-1.95 (1H, m).

Workup

  1. temperatureUpon cooling to room temperature
  2. customthe tarrified reaction mixture
  3. washwashed with saturated aqueous solution of sodium bicarbonate
  4. customThe organic layer was separated
  5. extractionthe aqueous layer was extracted with ethyl acetate
  6. dry with materialThe combined organic extracts were dried over anhydrous magnesium sulfate
  7. filtrationfiltered
  8. customThe solvent was removed in vacuum
  9. customthe residue was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-1ddc89d748eb48d290429d6e41675e1b
Source dataset
uspto-grants-2014_01
Patent number
US08637525B2

Reaction notes

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