Cesium carbonate → 4-(3-chloropropyl)-2H-1,4-benzoxazin-3(4H)-one

HRID 1191507Notes

Reaction equation

HRID 1191507 reaction equation
[O:1]1[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[NH:4][C:3](=[O:11])[CH2:2]1.[Cl:12][CH2:13][CH2:14][CH2:15]I.C([O-])([O-])=O.[Cs+].[Cs+]>CC#N>[Cl:12][CH2:13][CH2:14][CH2:15][N:4]1[C:5]2[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=2[O:1][CH2:2][C:3]1=[O:11]

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 727572H-1,4-benzoxazin-3(4H)-oneHCID 813631-Chloro-3-iodopropane

Product 1

HCID 233451504-(3-chloropropyl)-2H-1,4-benzoxazin-3(4H)-oneYield 88%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A reaction flask was charged with 4H-benzo[1,4]oxazin-3-one (1.48 g, 10 mmol), 1-chloro-3-iodopropane (2.04 g, 10 mmol), and Cs2CO3 (4.88 g, 15 mmol) in MeCN (10 mL) and stirred at rt for 40 h. The reaction mixture was quenched with water and the product extracted into EtOAc. The combined organic phases were dried over Na2SO4, filtered, and concentrated. The product was purified by flash column chromatography (SiO2; n-heptane/EtOAc 2:1) to give the title compound (1.97 g, 88%). 1H NMR (CDCl3) δ 7.06-7.02 (m, 2H), 7.01-6.99 (m, 2H), 4.58 (s, 2H), 4.12-4.07 (m, 2H), 3.64-3.60 (m, 2H), 2.19-2.12 (m, 2); 13C NMR (CDCl3) δ 164.7, 145.6, 128.6, 124.2, 123.2, 117.5, 114.9, 67.8, 42.6, 39.1, 30.3.

Workup

  1. customThe reaction mixture was quenched with water
  2. extractionthe product extracted into EtOAc
  3. dry with materialThe combined organic phases were dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe product was purified by flash column chromatography (SiO2; n-heptane/EtOAc 2:1)

Sources & evidence

ORD record
ord-ebf8cc2ad1e94f10893b916775f4d87f
Source dataset
uspto-grants-2014_03
Patent number
US08680115B2

Reaction notes

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