Hydrochloric Acid → 3-(2,4-Bis(dimethylamino)phenyl)-3-(2-ethoxy-4-(diethylamino)phenyl)phthalide

HRID 1707141

Reaktionsgleichung

Reaktionsgleichung von HRID 1707141
[CH2:1]([O:3][C:4]1[CH:20]=[C:19]([N:21]([CH2:24][CH3:25])[CH2:22][CH3:23])[CH:18]=[CH:17][C:5]=1[C:6]([C:8]1[CH:16]=[CH:15][CH:14]=[CH:13][C:9]=1[C:10](O)=[O:11])=[O:7])[CH3:2].[CH3:26][N:27]([CH3:37])[C:28]1[CH:33]=[CH:32][CH:31]=[C:30]([N:34]([CH3:36])[CH3:35])[CH:29]=1.C(OC(=O)C)(=O)C.Cl>>[CH3:35][N:34]([CH3:36])[C:30]1[CH:29]=[C:28]([N:27]([CH3:37])[CH3:26])[CH:33]=[CH:32][C:31]=1[C:6]1([C:5]2[CH:17]=[CH:18][C:19]([N:21]([CH2:22][CH3:23])[CH2:24][CH3:25])=[CH:20][C:4]=2[O:3][CH2:1][CH3:2])[C:8]2[C:9](=[CH:13][CH:14]=[CH:15][CH:16]=2)[C:10](=[O:11])[O:7]1

Komponenten

5

Edukt 4

HCID 313Hydrochloric AcidHCID 7918Acetic AnhydrideHCID 897151,3-Benzenediamine, N1,N1,N3,N3-tetramethyl-HCID 155193322-[4-(Diethylamino)-2-ethoxybenzoyl]benzoic acid

Produkt 1

HCID 233433633-(2,4-Bis(dimethylamino)phenyl)-3-(2-ethoxy-4-(diethylamino)phenyl)phthalide

Versuchsvorschrift

A mixture of 2-(2-ethoxy-4-(diethylamino)benzoyl)benzoic acid (6.82 g.), N,N,N',N'-tetramethyl-m-phenylenediamine (2.80 g.) and acetic anhydride (20 g.) was heated (70°-75° C.) during one hour, let stand overnight and poured into dilute hydrochloric acid. The resulting mixture was basified. Recrystallization of the resulting red precipitate from hexane followed by slurrying in alkaline water afforded 3-(2,4-bis(dimethylamino)phenyl)-3-(2-ethoxy-4-(diethylamino)phenyl)phthalide (I: X=(CH3)2N, Y2 =CH3CH2O, Y4 =(CH3CH2)2N, Z4 =Z5 =Z6 =Z7 =H) (m.p. 146°-150° C.).

Aufarbeitung

  1. temperaturewas heated (70°-75° C.) during one hour
  2. customRecrystallization of the resulting red precipitate from hexane

Quellen und Nachweise

ORD-Eintrag
ord-dcef943abfe04a4ca37063fd45ee23e7
Quelldatensatz
uspto-grants-1980_06
Patentnummer
US04209618

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