Cesium carbonate → HCID 68908046, compound

HRID 1191504Notes

Reaction equation

HRID 1191504 reaction equation
[CH2:1]([C:3]1[C:12]2[O:11][CH2:10][C:9](=[O:13])[NH:8][C:7]=2[CH:6]=[CH:5][CH:4]=1)[CH3:2].C([O-])([O-])=O.[Cs+].[Cs+].[Cl:20][CH2:21][CH2:22][CH2:23]I>>[Cl:20][CH2:21][CH2:22][CH2:23][N:8]1[C:7]2[CH:6]=[CH:5][CH:4]=[C:3]([CH2:1][CH3:2])[C:12]=2[O:11][CH2:10][C:9]1=[O:13]

Participants

4

Reactant 3

HCID 10796Cesium carbonateHCID 813631-Chloro-3-iodopropaneHCID 68908542HCID 68908542, compound

Product 1

HCID 68908046HCID 68908046, compoundYield 74.9%

Procedure

8-Ethyl-4H-benzo[1,4]oxazin-3-one (0.35 g, 2.0 mmol), Cs2CO3 (0.96 g, 2.9 mmol), and 1-chloro-3-iodopropane (0.45 g, 2.2 mmol) were mixed according to GP2. Purified by column chromatography (SiO2; heptanes/EtOAc, gradient 0 to 50% EtOAc) to give the title compound (0.38 g, 74%). Rf=0.64 (heptanes/EtOAc 1:1); 1H NMR (CDCl3) δ 7.01-6.89 (m, 2H), 4.58 (s, 2H), 4.12-4.07 (m, 2H), 3.62 (t, J=6.4 Hz, 2H), 2.65 (q, J=7.6 Hz, 2H), 2.21-2.12 (m, 2H), 1.20 (t, J=7.6 Hz, 3H); 13C NMR (CDCl3) δ 164.9, 143.3, 133.4, 128.4, 124.3, 122.6, 112.6, 67.2, 42.5, 39.2, 30.3, 23.0, 14.5.

Workup

  1. customPurified by column chromatography (SiO2; heptanes/EtOAc, gradient 0 to 50% EtOAc)

Sources & evidence

ORD record
ord-9d5f6b420f124befadb91f5318bd5ac2
Source dataset
uspto-grants-2014_03
Patent number
US08680115B2

Reaction notes

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