Cesium carbonate → HCID 68908176, compound

HRID 2103185Notes

Reaction equation

HRID 2103185 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([CH3:13])[C:5]2[O:10][CH2:9][C:8](=[O:11])[NH:7][C:6]=2[CH:12]=1.C([O-])([O-])=O.[Cs+].[Cs+].[Cl:20][CH2:21][CH2:22][CH2:23]I>CCCCCCC.CCOC(C)=O>[Cl:20][CH2:21][CH2:22][CH2:23][N:7]1[C:6]2[CH:12]=[C:2]([CH3:1])[CH:3]=[C:4]([CH3:13])[C:5]=2[O:10][CH2:9][C:8]1=[O:11]

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 813631-Chloro-3-iodopropaneHCID 14174150HCID 14174150, compound

Product 1

HCID 68908176HCID 68908176, compoundYield 39.4%

Reagents, catalysts & solvents 1

HCID 21899848Ethylacetate heptaneSolvent

Procedure

6,8-Dimethyl-4H-benzo[1,4]oxazin-3-one (81MF2237a) (1.70 g, 9.60 mmol), Cs2CO3 (4.69 g, 14.4 mmol) and 3-chloro-1-iodopropane (2.15 g, 10.6 mmol) were mixed according to GP6. CC (SiO2; Heptane/EtOAc 10:1-5) gave the title compound (81MF2237b) (0.96 g, 39%). 1H NMR (CDCl3) δ 6.72-6.69 (m, 2H), 4.56 (s, 2H), 4.07 (t, 2H), 3.62 (t, J=6.4 Hz, 2H), 2.30 (s, 3H), 2.20 (s, 3H), 2.19-2.12 (m, 2H); 13C NMR (CDCl3) δ 164.9, 141.5, 131.9, 128.0, 126.7, 126.4, 113.1, 67.8, 42.5, 39.0, 30.3, 21.2, 15.5.

Sources & evidence

ORD record
ord-c51f486df9604008a9469991f5b83491
Source dataset
uspto-grants-2009_08
Patent number
US07576100B2

Reaction notes

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