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

HRID 2102524Notes

Reaction equation

HRID 2102524 reaction equation
[F: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>>[Cl:19][CH2:20][CH2:21][CH2:22][N:6]1[C:5]2[CH:11]=[CH:12][C:2]([F:1])=[CH:3][C:4]=2[O:9][CH2:8][C:7]1=[O:10]

Participants

4

Reactant 3

HCID 10796Cesium carbonateHCID 813631-Chloro-3-iodopropaneHCID 137312957-fluoro-3,4-dihydro-2H-1,4-benzoxazin-3-one

Product 1

HCID 688939964-(3-Chloropropyl)-7-fluoro-4H-benzo[1,4]oxazin-3-oneYield 104.6%

Procedure

7-Fluoro-4H-benzo[1,4]oxazin-3-one (81MF763) (0.263 g, 1.57 mmol), Cs2CO3 (0.769 g, 2.36 mmol) and 3-chloro-1-iodopropane (0.354 g, 1.73 mmol) were mixed according to GP5 giving the crude title compound (0.40 g); 1H NMR (CDCl3) δ 7-01-6.91 (m, 1H), 6.79-6.73 (m, 2H), 4.60 (s, 2H), 4.08 (t, J=7.2 Hz, 2H), 3.62 (t, J=6.4 Hz, 2H), 2.18-2.11 (m, 2H).

Sources & evidence

ORD record
ord-58dbca1bac0b4620b1863630a84e2a8f
Source dataset
uspto-grants-2009_08
Patent number
US07576078B2

Reaction notes

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