Isocyanatocarbonyl chloride → HCID 58075467, compound

HRID 2370159Notes

Reaction equation

HRID 2370159 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:9]2[CH2:13][CH2:12][CH2:11][C:10]2=[O:14])[CH:5]=[CH:6][C:7]=1[F:8].[C:15](Cl)([N:17]=[C:18]=[O:19])=[O:16]>C(OCC)(=O)C>[F:1][C:2]1[CH:3]=[C:4]([CH:9]2[C:10]3[O:14][C:18](=[O:19])[NH:17][C:15](=[O:16])[C:11]=3[CH2:12][CH2:13]2)[CH:5]=[CH:6][C:7]=1[F:8]

Participants

4

Reactant 2

HCID 119708Isocyanatocarbonyl chlorideHCID 628023552-(3,4-Difluorophenyl)cyclopentanone

Product 1

HCID 58075467HCID 58075467, compoundYield 51.8%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
130 °C

Procedure

A solution of 2-(3,4-difluorophenyl)cyclopentanone, (prepared in the manner of Intermediate P(1) and P(2)) (1.5 g, 7.65 mmol) and carbonisocyanatidic chloride (1.129 g, 10.70 mmol) was stirred at 58° C. in a high-pressure vessel for 1 h. The temperature was raised to 130° C. and the reaction mixture was stirred for an additional 2 h. After cooling to rt, the reaction mixture solidified. The solid residue 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 twice with ethyl acetate. The combined organic extracts were dried over anhydrous sodium sulfate and filtered. The solvent was removed in vacuum and the oily residue was purified by column chromatography on silica gel to provide 7-(3,4-difluorophenyl)-6,7-dihydrocyclopenta[e][1,3]oxazine-2,4(3H,5H)-dione (1.05 g, 3.96 mmol, 51.8% yield) as a white solid. 1H NMR (500 MHz, CDCl3) δ ppm 8.16 (1H, br s), 7.15 (1H, dt, J=10.0, 8.3 Hz), 6.97-7.05 (1H, m), 6.88-6.95 (1H, m), 2.80-2.90 (1H, m), 2.61-2.78 (2H, m), 0.78-0.86 (2H, m).

Workup

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

Sources & evidence

ORD record
ord-158cb1c47715440a84688546047a2fd1
Source dataset
uspto-grants-2014_04
Patent number
US08710061B2

Reaction notes

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