Cesium carbonate → HCID 68911066, compound

HRID 2102522Notes

Reaction equation

HRID 2102522 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[C:3]=1[F:13].C([O-])([O-])=O.[Cs+].[Cs+].[Cl:20][CH2:21][CH2:22][CH2:23]I>>[Cl:20][CH2:21][CH2:22][CH2:23][N:6]1[C:5]2[CH:11]=[CH:12][C:2]([F:1])=[C:3]([F:13])[C:4]=2[O:9][CH2:8][C:7]1=[O:10]

Participants

4

Reactant 3

HCID 10796Cesium carbonateHCID 813631-Chloro-3-iodopropaneHCID 592983827,8-Difluoro-2H-1,4-benzoxazin-3(4H)-one

Product 1

HCID 68911066HCID 68911066, compoundYield 93.2%

Procedure

7,8-Difluoro-4H-benzo[1,4]oxazin-3-one (81MF2082a) (0.119 g, 0.64 mmol), Cs2CO3 (0.314 g, 0.96 mmol) and 3-chloro-1-iodopropane (0.144 g, 0.70 mmol) were mixed according to GP5 giving the crude title compound (0.156 g); 1H NMR (CDCl3) δ 6.89-6.82 (m, 1H), 6.78-6.74 (m, 1H), 4.68 (s, 2H), 4.08 (t, J=7.2 Hz, 2H), 3.62 (t, J=6.4 Hz, 2H), 2.18-2.10 (m, 2H); 13CNMR (CDCl3) δ 163.5, 147.7 (q, J=245.6 Hz, J=10.4 Hz), 141.0 (q, J=249.4 Hz, J=15.7 Hz), 135.5, 126.2, 109.9 (d, J=18.4 Hz), 108.6 (q, J=7.6 Hz, J=4.2 Hz), 67.8, 42.3, 39.4, 30.0.

Sources & evidence

ORD record
ord-3a8ed704cc114540b085c176b9c18489
Source dataset
uspto-grants-2009_08
Patent number
US07576078B2

Reaction notes

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