Phthalic Anhydride → 2-[3-(4-Chlorobenzoyl)-4,5-dimethylthiophen-2-yl]isoindole-1,3-dione

HRID 597827ノート

反応式

HRID 597827 の反応式
[NH2:1][C:2]1[S:3][C:4]([CH3:17])=[C:5]([CH3:16])[C:6]=1[C:7]([C:9]1[CH:14]=[CH:13][C:12]([Cl:15])=[CH:11][CH:10]=1)=[O:8].[C:18]1(=O)[O:23][C:21](=[O:22])[C:20]2=[CH:24][CH:25]=[CH:26][CH:27]=[C:19]12>C(O)(=O)C>[Cl:15][C:12]1[CH:13]=[CH:14][C:9]([C:7]([C:6]2[C:5]([CH3:16])=[C:4]([CH3:17])[S:3][C:2]=2[N:1]2[C:21](=[O:22])[C:20]3[C:19](=[CH:27][CH:26]=[CH:25][CH:24]=3)[C:18]2=[O:23])=[O:8])=[CH:10][CH:11]=1

参加物

4

反応物 2

HCID 6811Phthalic AnhydrideHCID 719710(2-Amino-4,5-dimethylthiophen-3-yl)(4-chlorophenyl)methanone

生成物 1

HCID 574339032-[3-(4-Chlorobenzoyl)-4,5-dimethylthiophen-2-yl]isoindole-1,3-dione

試薬・触媒・溶媒 1

HCID 176Acetic Acid溶媒

実験手順

To a solution of (2-amino-4,5-dimethylthiophen-3-yl)(4-chlorophenyl)methanone (532 mg, 2 mmol; prepared as described in U.S. Pat. No. 6,323,214) in acetic acid (15 mL) is added phthalic anhydride (360 mg, 2.4 mmol) and the mixture is heated to reflux for 15 h. The solvent is evaporated in vacuo and the residual material is dissolved in ethyl acetate (20 mL). The organic solution is washed with a saturated aqueous solution of NaHCO3 (5 mL), water (5 mL), then brine (5 mL), dried (Na2SO4), filtered, and concentrated in vacuo. The crude product is stirred for 1 h in petroleum ether (20 mL), then filtered, affording (2-[3-(4-chlorobenzoyl)-4,5-dimethylthiophen-2-yl]isoindoline-1,3-dione as a yellow powder. 1H NMR (CDCl3) δ: 2.10 (s, 3H), 2.43 (s, 3H), 7.24 (d, J=8.4 Hz, 2H), 7.64 (d, J=8.4 Hz, 2H), 7.78 (m, 4H).

後処理

  1. customprepared
  2. temperaturethe mixture is heated
  3. temperatureto reflux for 15 h
  4. customThe solvent is evaporated in vacuo
  5. dissolutionthe residual material is dissolved in ethyl acetate (20 mL)
  6. washThe organic solution is washed with a saturated aqueous solution of NaHCO3 (5 mL), water (5 mL)
  7. dry with materialbrine (5 mL), dried (Na2SO4)
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo
  10. filtrationfiltered

出典と根拠

ORDレコード
ord-efca790dd2da49f2bf31a62dc1694e1d
出典データセット
uspto-grants-2011_03
特許番号
US07897596B2

反応ノート

読み込み中…