Isocyanatocarbonyl chloride → 4-(2,4-Dioxo-2,3,4,5,7,8-hexahydropyrano[3,4-e][1,3]oxazin-8-yl)benzonitrile

HRID 2370201Notes

Reaction equation

HRID 2370201 reaction equation
[O:1]=[C:2]1[CH2:7][CH2:6][O:5][CH2:4][CH:3]1[C:8]1[CH:15]=[CH:14][C:11]([C:12]#[N:13])=[CH:10][CH:9]=1.[C:16](Cl)([N:18]=[C:19]=[O:20])=[O:17]>>[O:17]=[C:16]1[NH:18][C:19](=[O:20])[C:7]2[CH2:6][O:5][CH2:4][CH:3]([C:8]3[CH:15]=[CH:14][C:11]([C:12]#[N:13])=[CH:10][CH:9]=3)[C:2]=2[O:1]1

Participants

3

Reactant 2

HCID 119708Isocyanatocarbonyl chlorideHCID 580755704-(4-oxotetrahydro-2H-pyran-3-yl)benzonitrile

Product 1

HCID 580754234-(2,4-Dioxo-2,3,4,5,7,8-hexahydropyrano[3,4-e][1,3]oxazin-8-yl)benzonitrile

Procedure

4-(4-oxotetrahydro-2H-pyran-3-yl)benzonitrile (Intermediate AA(2)) was reacted as described in Intermediate X(3) with carbonisocyanatidic chloride to give 4-(2,4-dioxo-2,3,4,5,7,8-hexahydropyrano[3,4-e][1,3]oxazin-8-yl)benzonitrile (Intermediate AA(3)). LC-MS (M+H)+=271.1. 1H NMR (400 MHz, CDCl3) δ ppm 7.57-7.78 (m, 2 H) 7.41-7.51 (m, 2 H) 4.61-4.75 (m, 1 H) 4.50 (dd, J=15.49, 2.14 Hz, 1 H) 4.04-4.20 (m, 2 H) 3.78 (br. s., 1 H).

Sources & evidence

ORD record
ord-124047d4369447aea1c3f1785101960e
Source dataset
uspto-grants-2014_04
Patent number
US08710061B2

Reaction notes

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