Isocyanatocarbonyl chloride → 8-(4-fluorophenyl)-5,6,7,8-tetrahydro-2H-benzo[e][1,3]oxazine-2,4(3H)-dione

HRID 475843Notes

Reaction equation

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

Participants

Reactant 2

HCID 119708Isocyanatocarbonyl chloride

HCID 130895402-(4-Fluorophenyl)cyclohexan-1-one

Product 1

HCID 580756508-(4-fluorophenyl)-5,6,7,8-tetrahydro-2H-benzo[e][1,3]oxazine-2,4(3H)-dioneYield 19.62%

Procedure

2-(4-fluorophenyl)cyclohexanone and carbonisocyanatidic chloride (0.966 mL, 12 mmol) was reacted as in Intermediate AC(1) to provide 8-(4-fluorophenyl)-5,6,7,8-tetrahydro-2H-benzo[e][1,3]oxazine-2,4(3H)-dione (415.0 mg, 1.689 mmol, 19.62% yield) as white solid and 4a-(4-fluorophenyl)-4-a,5,6,7-tetrahydro-2H-benzo[e][1,3]oxazine-2,4(3H)-dione (746.4 mg, 3.04 mmol, 35.3% yield) as white solid.

Sources & evidence

ORD record: ord-842ae71aa35d407695d1bb5247d737cd
Source dataset: uspto-grants-2014_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08637525B2

Reaction notes

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