2,3-Benzofurandione → HCID 23043607, compound

HRID 2165101Notes

Reaction equation

HRID 2165101 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[C:3](=[O:10])[C:2]1=[O:11].[NH2:12][C:13]1[CH:18]=[CH:17][C:16]([CH2:19][CH2:20][C:21]2[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[C:23]([O:29][CH3:30])[CH:22]=2)=[CH:15][CH:14]=1>O1CCCC1>[CH3:30][O:29][C:23]1[CH:22]=[C:21]([CH2:20][CH2:19][C:16]2[CH:15]=[CH:14][C:13]([NH:12][C:2](=[O:11])[C:3](=[O:10])[C:4]3[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=3[OH:1])=[CH:18][CH:17]=2)[CH:26]=[CH:25][C:24]=1[O:27][CH3:28]

Participants

4

Reactant 2

HCID 1383332,3-BenzofurandioneHCID 142560244-(3,4-Dimethoxyphenethyl)aniline

Product 1

HCID 23043607HCID 23043607, compoundYield 90.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 2,3-benzofurandione (Fries and Pfaffendorf, Ber, 45, 156 (1912); Valentine, Titoff, Muller, and Reichstein, Helv. Chim. Acta, 20, 883 (1937)) (10 g, 0.0675 mol) and 4-[2-(4-aminophenyl)ethyl]-1,2-dimethoxybenzene (15.6 g, 0.0606 mol) in dry tetrahydrofuran is stirred at room temperature under nitrogen for 18 hours in the dark. The solvent is removed under reduced pressure on a rotary evaporator below 35° and the resulting solid is recrystallized from tetrahydrofuran-ethanol to give 22.2 g (90.6%) of a light-yellow solid, mp 124°-125° C.

Workup

  1. customThe solvent is removed under reduced pressure on a rotary evaporator below 35°
  2. customthe resulting solid is recrystallized from tetrahydrofuran-ethanol

Sources & evidence

ORD record
ord-af81dc8c2b8b4f17ae91a358456997cf
Source dataset
uspto-grants-1990_07
Patent number
US04939133

Reaction notes

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