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

HRID 597827노트

반응식

HRID 597827 반응식
[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

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 176Acetic Acid용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-efca790dd2da49f2bf31a62dc1694e1d
출처 데이터셋
uspto-grants-2011_03
특허 번호
US07897596B2

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