Acetic Anhydride → 3-(2,4-Bis(diethylamino)phenyl)-3-(2-methyl-4-(diethylamino)phenyl)phthalide

HRID 27024

Reaktionsgleichung

Reaktionsgleichung von HRID 27024
[CH3:1][C:2]1[CH:18]=[C:17]([N:19]([CH2:22][CH3:23])[CH2:20][CH3:21])[CH:16]=[CH:15][C:3]=1[C:4]([C:6]1[CH:14]=[CH:13][CH:12]=[CH:11][C:7]=1[C:8](O)=[O:9])=[O:5].[CH2:24]([N:26]([CH2:38][CH3:39])[C:27]1[CH:32]=[CH:31][CH:30]=[C:29]([N:33]([CH2:36][CH3:37])[CH2:34][CH3:35])[CH:28]=1)[CH3:25].C(OC(=O)C)(=O)C>O>[CH2:36]([N:33]([CH2:34][CH3:35])[C:29]1[CH:28]=[C:27]([N:26]([CH2:38][CH3:39])[CH2:24][CH3:25])[CH:32]=[CH:31][C:30]=1[C:4]1([C:3]2[CH:15]=[CH:16][C:17]([N:19]([CH2:22][CH3:23])[CH2:20][CH3:21])=[CH:18][C:2]=2[CH3:1])[C:6]2[C:7](=[CH:11][CH:12]=[CH:13][CH:14]=2)[C:8](=[O:9])[O:5]1)[CH3:37]

Komponenten

5

Edukt 3

HCID 7918Acetic AnhydrideHCID 1043352-(4-(Diethylamino)-2-methylbenzoyl)benzoic acidHCID 19382815N~1~,N~1~,N~3~,N~3~-Tetraethylbenzene-1,3-diamine

Produkt 1

HCID 867348983-(2,4-Bis(diethylamino)phenyl)-3-(2-methyl-4-(diethylamino)phenyl)phthalide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

A mixture of 2-(2-methyl-4-(diethylamino)benzoyl)benzoic acid (12.48 g.), N,N,N',N'-tetraethyl-m-phenylenediamine (10.56 g.) and acetic anhydride (12 ml.) was warmed (at 40°±8° C.) during one hour, diluted with water (50 ml., then 100 ml.), adjusted to pH 4.6 and filtered. The filtrate was clarified with water and adjusted to pH 5.5. Recrystallization of the resulting product (m.p. 134°-140° C.) from methanol afforded 3-(2,4-bis(diethylamino)phenyl)-3-(2-methyl-4-(diethylamino)phenyl)phthalide (I: X=Y4 =(CH3CH2)2N, Y2 =CH3, Z4 =Z5 =Z6 =Z7 =H) (m.p. 149°-151° C.).

Aufarbeitung

  1. temperaturewas warmed (at 40°±8° C.) during one hour
  2. filtrationfiltered
  3. customRecrystallization of the resulting product (m.p. 134°-140° C.) from methanol

Quellen und Nachweise

ORD-Eintrag
ord-fa66cc458c26455bb8925a70dd2f5bc7
Quelldatensatz
uspto-grants-1980_09
Patentnummer
US04220357

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