반응 #685009

반응 방정식

(2-amino-4,5-dimethylthiophen-3-yl)(4-chlorophenyl)methanone

phthalic anhydride

→

2-[3-(4-chlorobenzoyl)-4,5-dimethylthiophen-2-yl]isoindoline-1,3-dione

용매

acetic acid

반응 조건

후처리

1. 1
   기타prepared
2. 2
   온도the mixture is heated
3. 3
   온도to reflux for 15 h
4. 4
   기타The solvent is evaporated in vacuo
5. 5
   workup.DISSOLUTIONthe residual material is dissolved in ethyl acetate (20 mL)
6. 6
   세척The organic solution is washed with a saturated aqueous solution of NaHCO3 (5 mL), water (5 mL)
7. 7
   건조brine (5 mL), dried (Na2SO4)
8. 8
   여과filtered
9. 9
   농축concentrated in vacuo
10. 10
    여과filtered

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).

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