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

HRID 27018

Reaction equation

HRID 27018 reaction equation
[CH3:1][N:2]([CH3:27])[C:3]1[CH:23]=[C:22]([N:24]([CH3:26])[CH3:25])[CH:21]=[CH:20][C:4]=1[C:5]([C:7]1[C:15]([Cl:16])=[C:14]([Cl:17])[C:13]([Cl:18])=[C:12]([Cl:19])[C:8]=1[C:9](O)=[O:10])=[O:6].[CH3:28][N:29]([CH3:39])[C:30]1[CH:35]=[CH:34][CH:33]=[C:32]([N:36]([CH3:38])[CH3:37])[CH:31]=1.C(OC(=O)C)(=O)C>CCCCCC>[CH3:37][N:36]([CH3:38])[C:32]1[CH:31]=[C:30]([N:29]([CH3:39])[CH3:28])[CH:35]=[CH:34][C:33]=1[C:5]1([C:4]2[CH:20]=[CH:21][C:22]([N:24]([CH3:26])[CH3:25])=[CH:23][C:3]=2[N:2]([CH3:27])[CH3:1])[C:7]2[C:8](=[C:12]([Cl:19])[C:13]([Cl:18])=[C:14]([Cl:17])[C:15]=2[Cl:16])[C:9](=[O:10])[O:6]1

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 897151,3-Benzenediamine, N1,N1,N3,N3-tetramethyl-HCID 233433732-(2,4-Bis(dimethylamino)benzoyl)-3,4,5,6-tetrachlorobenzoic acid

Product 1

HCID 233433603,3-Bis(2,4-bis(dimethylamino)phenyl)-4,5,6,7-tetrachlorophthalide

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

A mixture of most of the 2-(2,4-bis(dimethylamino)benzoyl)-3,4,5,6-tetrachlorobenzoic acid from part A of this example, N,N,N',N'-tetramethyl-m-phenylenediamine (0.82 g. plus 0.4 g.) and acetic anhydride was heated under reflux. Concentration of a toluene extract of the resulting product gave a tar, which was slurried in hexane, affording 3,3-bis(2,4-bis(dimethylamino)phenyl)-4,5,6,7-tetrachlorophthalide (I: X=Y2 =Y4 =(CH3)2N, Z4 =Z5 =Z6 =Z7 =Cl) (m.p. 195°-197° C.).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux
  3. extractionConcentration of a toluene extract of the resulting product
  4. customgave a tar, which

Sources & evidence

ORD record
ord-91c7a50c823240d7bd5151d81de90b02
Source dataset
uspto-grants-1980_09
Patent number
US04220357

Linked notes

Loading…