Reaktion #1747461

Reaktionsgleichung

2-[(1-n-butyl-2-methyl-3-indolyl)carbonyl]-3,4,5,6-tetrachlorobenzoic acid

N,N,N',N'-tetramethyl-m-phenylenediamine

acetic anhydride

sodium hydroxide

→

3-[2,4-bis(dimethylamino)phenyl]-3-(1-n-butyl-2-methyl-3-indolyl)-4,5,6,7-tetrachlorophthalide

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturThe reaction mixture was then cooled to ambient temperature
2. 2
   Extraktionextracted with benzene
3. 3
   workup.ADDITIONPetroleum ether was slowly added to the separated benzene
4. 4
   Extraktionextract
5. 5
   Sonstigethe solid which slowly separated
6. 6
   Filtrationwas collected by filtration
7. 7
   Sonstigedried

Vorschrift

A mixture of 5.20 g (0.01 mole) of 2-[(1-n-butyl-2-methyl-3-indolyl)carbonyl]-3,4,5,6-tetrachlorobenzoic acid, prepared in part A above, 2.0 g (0.012 mole) of N,N,N',N'-tetramethyl-m-phenylenediamine and five ml of acetic anhydride was warmed over a period of approximately forty minutes at 110° C. The reaction mixture was then cooled to ambient temperature, set aside overnight, rendered alkaline with 10 percent aqueous sodium hydroxide solution and extracted with benzene. Petroleum ether was slowly added to the separated benzene extract and the solid which slowly separated was collected by filtration and dried to obtain 3-[2,4-bis(dimethylamino)phenyl]-3-(1-n-butyl-2-methyl-3-indolyl)-4,5,6,7-tetrachlorophthalide (Formula III: Ro =R1 =R2 =R3 =Cl; R=R5 =CH3 ; R4 =N(CH3)2 ; R6 =(CH2)3CH3 ; Y1 =H), as white crystals having a melting point of 173°-175° C. The nuclear magnetic resonance spectrum was consistent with the structure; a maximum of 1770 cm-1 (C=O; s) appeared in the infrared spectrum; the spectrum showed a m/e peak at 617 (M+, 4 Cl).

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