Isatoic Anhydride → N-propylisatoic anhydride

HRID 53256

反応式

HRID 53256 の反応式
[C:1]12[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=1)[NH:6][C:5](=[O:12])[O:4][C:2]2=[O:3].[CH2:13](I)[CH2:14][CH3:15].[H-].[Na+]>>[CH2:13]([N:6]1[C:5](=[O:12])[O:4][C:2](=[O:3])[C:1]2=[CH:11][CH:10]=[CH:9][CH:8]=[C:7]12)[CH2:14][CH3:15]

参加物

4

反応物 3

HCID 8359Isatoic AnhydrideHCID 24758Sodium hydrideHCID 336431-Iodopropane

生成物 1

HCID 3933296N-propylisatoic anhydride

実験手順

To a stirred solution of isatoic anhydride (100 g) and propyl iodide (66 ml) in dimethylfomamide (600 ml) at 0° C., under nitrogen, was added sodium hydride (28 g of a 55% dispersion in mineral oil) portionwise. The mixture was allowed to warm to room temperature and stirred for 18 h. The solvent was then removed in vacuo and the residue partitioned between ethyl acetate (1000 ml) and water (500 ml). The organic phase was separated, washed with brine (2×500 ml), dried (MgSO4) and evaporated. The residue was triturated with anhydrous diethyl ether to give the title compound (57 g). 1H NMR (360 MHz, CDCl3) δ1.06 (3H, t, J=7.5 Hz), 1.75-1.86 (2H, m), 4.01-4.05 (2H, m), 7.17 (1H, d, J=8.5 Hz), 7.26-7.32 (1H, m), 7.73-7.78 (1H, m), 8.17 (1H, dd, J=7.9 and 1.7 Hz). MS (CI) m/e 205 [MH]+.

後処理

  1. customThe solvent was then removed in vacuo
  2. customthe residue partitioned between ethyl acetate (1000 ml) and water (500 ml)
  3. customThe organic phase was separated
  4. washwashed with brine (2×500 ml)
  5. dry with materialdried (MgSO4)
  6. customevaporated
  7. customThe residue was triturated with anhydrous diethyl ether

出典と根拠

ORDレコード
ord-0432be68ecb348b0a5947b64efdfec62
出典データセット
uspto-grants-1997_04
特許番号
US05618812

関連ノート

読み込み中…