Cesium carbonate → 4-(3-Chloropropyl)-8-isopropyl-4H-benzo[1,4]oxazin-3-one

HRID 2103178Notes

Reaction equation

HRID 2103178 reaction equation
[CH:1]([C:4]1[C:13]2[O:12][CH2:11][C:10](=[O:14])[NH:9][C:8]=2[CH:7]=[CH:6][CH:5]=1)([CH3:3])[CH3:2].C([O-])([O-])=O.[Cs+].[Cs+].[Cl:21][CH2:22][CH2:23][CH2:24]I>CCCCCCC.CCOC(C)=O>[Cl:21][CH2:22][CH2:23][CH2:24][N:9]1[C:8]2[CH:7]=[CH:6][CH:5]=[C:4]([CH:1]([CH3:3])[CH3:2])[C:13]=2[O:12][CH2:11][C:10]1=[O:14]

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 813631-Chloro-3-iodopropaneHCID 689121768-Isopropyl-4H-benzo[1,4]oxazin-3-one

Product 1

HCID 689126914-(3-Chloropropyl)-8-isopropyl-4H-benzo[1,4]oxazin-3-oneYield 70%

Reagents, catalysts & solvents 1

HCID 21899848Ethylacetate heptaneSolvent

Procedure

8-Isopropyl-4H-benzo[1,4]oxazin-3-one (95MF83) (0.115 g, 0.60 mmol), Cs2CO3 (0.293 g, 0.90 mmol) and 3-chloro-1-iodopropane (0.135 g, 0.66 mmol) were mixed according to GP5. CC (SiO2; Heptane/EtOAc 9:1-4) gave the title compound (95MF98) (0.112 g, 70%). 1H NMR (CDCl3) δ 7.03-6.95 (m, 2H), 6.93-6.90 (m, 1H), 4.57 (s, 2H), 4.09 (m, 2H), 3.62 (t, J=6.2 Hz, 2H), 3.33-3.25 (m, 1H), 2.20-2.13 (m, 2H), 1.22 (d, J=7.2 Hz, 6H); 13CNMR(CDCl3) δ 164.9, 142.8, 137.8, 128.5, 122.8, 121.4, 112.5, 67.7, 42.5, 39.3, 30.3, 27.2, 22.7.

Sources & evidence

ORD record
ord-ca45336cd26a4b8da716e583bb426b81
Source dataset
uspto-grants-2009_08
Patent number
US07576100B2

Reaction notes

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