Isocyanatocarbonyl chloride → HCID 67393883, compound

HRID 451128Notes

Reaction equation

HRID 451128 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.[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]23[CH2:13][CH2:12][CH2:11][CH:10]=[C:9]2[O:14][C:18](=[O:19])[NH:17][C:15]3=[O:16])=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 119708Isocyanatocarbonyl chlorideHCID 130895402-(4-Fluorophenyl)cyclohexan-1-one

Product 2

HCID 580756508-(4-fluorophenyl)-5,6,7,8-tetrahydro-2H-benzo[e][1,3]oxazine-2,4(3H)-dioneYield 19.62%HCID 67393883HCID 67393883, compoundYield 35.3%

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)-4a,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. 8-(4-fluorophenyl)-5,6,7,8-tetrahydro-2H-benzo[e][1,3]oxazine-2,4(3H)-dione. LC-MS (M+H)+=262.1. 1H NMR (500 MHz, CDCl3) δ ppm 9.61 (1H, br s), 7.10 (2H, dd, J=5.0, 8.5 Hz), 6.98 (2H, app t, J=8.5 Hz), 3.77 (1H, t, J=4.9 Hz), 2.38-2.53 (2H, m), 2.16-2.07 (1H, m), 1.87-1.62 (3H, m).

Sources & evidence

ORD record
ord-b585a22b08674cbfbea883a9ec848fd9
Source dataset
uspto-grants-2013_07
Patent number
US08486952B2

Reaction notes

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