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

HRID 27025Notes

Reaction equation

HRID 27025 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.[CH3:25][N:26]([CH3:36])[C:27]1[CH:32]=[CH:31][CH:30]=[C:29]([N:33]([CH3:35])[CH3:34])[CH:28]=1.C(OC(=O)C)(=O)C>>[CH3:34][N:33]([CH3:35])[C:29]1[CH:28]=[C:27]([N:26]([CH3:36])[CH3:25])[CH:32]=[CH:31][C:30]=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

Participants

4

Reactant 3

HCID 7918Acetic AnhydrideHCID 897151,3-Benzenediamine, N1,N1,N3,N3-tetramethyl-HCID 20287184HCID 20287184, compound

Product 1

HCID 536562312,4-Bis(dimethylamino)phenyl-3-(4-(dimethylamino)phenyl)4,5,6,7-tetrachlorophthalideYield 73.6%

Conditions

Temperature
95 °C

Procedure

A mixture of 2-(4-(dimethylamino)benzoyl)-3,4,5,6-tetrachlorobenzoic acid (20.3 g.), N,N,N',N'-tetramethyl-m-phenylenediamine (88%, 9.3 g.) and acetic anhydride (74 ml.) was heated (to 95° C.) during one hour, then cooled, affording 3-(2,4-bis(dimethylamino)phenyl)-3-(4-(dimethylamino)phenyl)-4,5,6,7-tetrachlorophthalide (I: X=Y4 =(CH3)2N, Y2 =H, Z4 =Z5 =Z6 =Z7 =Cl) (20.3 g., m.p. 227°-229° C.).

Workup

  1. temperaturecooled

Sources & evidence

ORD record
ord-e7243038caf84dbb909518cc4f6fc1f6
Source dataset
uspto-grants-1980_09
Patent number
US04220357

Reaction notes

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