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

HRID 27028Notes

Reaction equation

HRID 27028 reaction equation
[CH3:1][N:2]([CH3:24])[C:3]1[CH:23]=[CH:22][C:6]([C:7]([C:9]2[C:17]([Cl:18])=[C:16]([Cl:19])[C:15]([Cl:20])=[C:14]([Cl:21])[C:10]=2[C:11]([OH:13])=O)=[O:8])=[CH:5][CH:4]=1.[CH2:25]([N:27]([CH2:39][CH3:40])[C:28]1[CH:33]=[CH:32][CH:31]=[C:30]([N:34]([CH2:37][CH3:38])[CH2:35][CH3:36])[CH:29]=1)[CH3:26].C(OC(=O)C)(=O)C>CO>[CH2:35]([N:34]([CH2:37][CH3:38])[C:30]1[CH:29]=[C:28]([N:27]([CH2:25][CH3:26])[CH2:39][CH3:40])[CH:33]=[CH:32][C:31]=1[C:7]1([C:6]2[CH:5]=[CH:4][C:3]([N:2]([CH3:24])[CH3:1])=[CH:23][CH:22]=2)[C:9]2[C:10](=[C:14]([Cl:21])[C:15]([Cl:20])=[C:16]([Cl:19])[C:17]=2[Cl:18])[C:11](=[O:13])[O:8]1)[CH3:36]

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 19382815N~1~,N~1~,N~3~,N~3~-Tetraethylbenzene-1,3-diamineHCID 20287184HCID 20287184, compound

Product 1

HCID 541421903-(2,4-Bis(diethylamino)phenyl)-3-(4-(dimethylamino)phenyl)-4,5,6,7-tetrachlorophthalide

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
91 °C

Procedure

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.).

Sources & evidence

ORD record
ord-e33a3d4516874e41849fd33164567e06
Source dataset
uspto-grants-1980_09
Patent number
US04220357

Reaction notes

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