Cesium carbonate → HCID 68910501, compound

HRID 2103188Notes

Reaction equation

HRID 2103188 reaction equation
[Cl: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:1][C:2]1[CH:12]=[CH:11][C:5]2[N:6]([CH2:22][CH2:21][CH2:20][Cl:19])[C:7](=[O:10])[CH2:8][O:9][C:4]=2[CH:3]=1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 813631-Chloro-3-iodopropaneHCID 118300867-Chloro-2H-1,4-benzoxazin

Product 1

HCID 68910501HCID 68910501, compoundYield 79.2%

Reagents, catalysts & solvents 1

HCID 21899848Ethylacetate heptaneSolvent

Procedure

7-Chloro-4H-benzo[1,4]oxazin-3-one (81MF2271a) (1.74 g, 9.47 mmol), Cs2CO3 (4.63 g, 14.2 mmol) and 3-chloro-1-iodopropane (2.13 g, 10.4 mmol) were mixed according to GP6. CC (SiO2; Heptane/EtOAc 10:1-5) gave the title compound (81MF2271b) (1.95 g, 79%). 1H NMR (CDCl3) δ 7.03-6.96 (m, 3H), 4.59 (s, 2H), 4.07 (t, J=7.2 Hz, 2H), 3.61 (t, J=6.4 Hz, 2H), 2.17-2.10 (m, 2H); 13C NMR (CDCl3) δ 164.0, 146.0, 129.1, 127.3, 123.0, 117.8, 115.5, 67.7, 42.4, 39.2, 30.0.

Sources & evidence

ORD record
ord-e5779b274f2b40d094d2fcecb21f8641
Source dataset
uspto-grants-2009_08
Patent number
US07576100B2

Reaction notes

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