Back
HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 27028Generated: October 26, 2026

Acetic Anhydride → 3-(2,4-Bis(diethylamino)phenyl)-3-(4-(dimethylamino)phenyl)-4,5,6,7-tetrachlorophthalide

https://huagongshe.com/reaction/27028

Reaction equation

Participants

RoleNameHCIDCharge
ReactantAcetic AnhydrideHCID 7918—
ReactantN~1~,N~1~,N~3~,N~3~-Tetraethylbenzene-1,3-diamineHCID 19382815—
ReactantHCID 20287184HCID 20287184—
SolventMethanolHCID 887—
Product3-(2,4-Bis(diethylamino)phenyl)-3-(4-(dimethylamino)phenyl)-4,5,6,7-tetrachlorophthalideHCID 54142190—

Reaction Conditions

Temperature91 °C

Reaction Steps

A mixture of 2-(4-(dimethylamino)benzoyl)-3,4,5,6-tetrachlorobenzoic acid (16.28 g.), N,N,N',N'-tetraethyl-m-phenylenediamine (9.68 g.) and acetic anhydride (10 ml.) was heated (at 91° C.) during two hours. Addition of methanol (20 ml., then 12 ml., then 10 ml.) afforded 3-(2,4-bis(diethylamino)phenyl)-3-(4-(dimethylamino)phenyl)-4,5,6,7-tetrachlorophthalide (I: X=(CH3CH2)2N, Y2 =H, Y4 =(CH3)2N, Z4 =Z5 =Z6 =Z7 =Cl) in three fractions (m.p. 174°-176° C., m.p. 180°-181° C. and m.p. 180°-181° C.).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS04220357
Source datasetuspto-grants-1980_09
ORD IDord-e33a3d4516874e41849fd33164567e06
Source noteuspto-grants-1980_09