Butyl bromide → Methyl 4-butyl-8-iodo-3-oxo-3,4-dihydro-2H-1,4-benzoxazine-6-carboxylate

HRID 14186

反応式

HRID 14186 の反応式
[I:1][C:2]1[C:11]2[O:10][CH2:9][C:8](=[O:12])[NH:7][C:6]=2[CH:5]=[C:4]([C:13]([O:15][CH3:16])=[O:14])[CH:3]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:24][CH2:25][CH2:26][CH3:27]>CS(C)=O.O>[CH2:24]([N:7]1[C:6]2[CH:5]=[C:4]([C:13]([O:15][CH3:16])=[O:14])[CH:3]=[C:2]([I:1])[C:11]=2[O:10][CH2:9][C:8]1=[O:12])[CH2:25][CH2:26][CH3:27]

参加物

6

反応物 3

HCID 8002Butyl bromideHCID 11430Potassium CarbonateHCID 21086219Methyl 8-iodo-3-oxo-3,4-dihydro-2H-1,4-benzoxazine-6-carboxylate

生成物 1

HCID 21086204Methyl 4-butyl-8-iodo-3-oxo-3,4-dihydro-2H-1,4-benzoxazine-6-carboxylate収率 72.6%

試薬・触媒・溶媒 2

HCID 679Dimethyl Sulfoxide溶媒HCID 962Water溶媒

反応条件

温度
80 °C

実験手順

To a solution of Methyl 8-iodo-3-oxo-3,4-dihydro-2H-1,4-benzoxazine-6-carboxylate (2.64 g) and potassium carbonate (5 g) in DMSO (20 mL) was added bromobutane (5 g), and the reaction mixture was stirred for 1 h at 80° C. The mixture was cooled to room temperature, diluted with 1:1 ethyl acetate/hexanes (100 mL) and water (160 mL), and separated. The organic layer was washed with water, and brine, dried (magnesium sulfate), filtered, and concentrated under reduced pressure. Purification by flash column chromatography (silica, 1:10 ethyl acetate/hexanes) afforded 2.24 g of the title compound: 1H NMR (300 MHz, CDCl3) δ 8.13, 7.63, 4.74, 3.96, 3.92, 1.64, 1.42, 0.97.

後処理

  1. temperatureThe mixture was cooled to room temperature
  2. customseparated
  3. washThe organic layer was washed with water, and brine
  4. dry with materialdried (magnesium sulfate)
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customPurification by flash column chromatography (silica, 1:10 ethyl acetate/hexanes)

出典と根拠

ORDレコード
ord-8bfa03f2629947919ce80c51d962cc90
出典データセット
uspto-grants-2010_06
特許番号
US07727997B2

関連ノート

読み込み中…