Cesium carbonate → 4-(3-Chloropropyl)-7-methyl-4H-benzo[1,4]oxazin-3-one

HRID 1191365Notes

Reaction equation

HRID 1191365 reaction equation
[CH3:1][C:2]1[CH:12]=[CH:11][C:5]2[NH:6][C:7](=[O:10])[CH2:8][O:9][C:4]=2[CH:3]=1.C([O-])([O-])=O.[Cs+].[Cs+].[Cl:19][CH2:20][CH2:21][CH2:22]I>CCCCCCC.CCOC(C)=O>[Cl:19][CH2:20][CH2:21][CH2:22][N:6]1[C:5]2[CH:11]=[CH:12][C:2]([CH3:1])=[CH:3][C:4]=2[O:9][CH2:8][C:7]1=[O:10]

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 813631-Chloro-3-iodopropaneHCID 3130987-Methyl-2H-1,4-benzoxazin-3(4H)-one

Product 1

HCID 689079504-(3-Chloropropyl)-7-methyl-4H-benzo[1,4]oxazin-3-oneYield 79%

Reagents, catalysts & solvents 1

HCID 21899848Ethylacetate heptaneSolvent

Procedure

7-Methyl-4H-benzo[1,4]oxazin-3-one (81MF2246a) (1.42 g, 8.7 mmol), Cs2CO3 (4.24 g, 13.0 mmol) and 3-chloro-1-iodopropane (1.95 g, 9.5 mmol) were mixed according to GP6. CC (SiO2; Heptane/EtOAc 10:1-5) gave the title compound (81MF2246b) (1.64 g, 79%). 1H NMR (CDCl3) δ 6.98-6.81 (m, 3H), 4.59 (s, 2H), 4.06-4.03 (m, 2H), 3.63-3.60 (m, 2H), 2.26 (s, 2H), 2.20-2.15 (m, 2H); 13C NMR (CDCl3) δ 164.8, 145.8, 134.3, 123.9, 118.1, 114.9, 68.0, 42.8, 39.4, 30.5, 21.0

Sources & evidence

ORD record
ord-174531e2b6374cf2986bbb4d8614c199
Source dataset
uspto-grants-2014_03
Patent number
US08680115B2

Reaction notes

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