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

HRID 839539

Reaktionsgleichung

Reaktionsgleichung von HRID 839539
[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 = Z 6 = 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-e6de2efb25294d94961b9e401015c4f2
Quelldatensatz
uspto-grants-1978_06
Patentnummer
US04096176

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