Acetic Anhydride → 3,3-Bis(2,4-bis(dimethylamino)phenyl)-5-(dimethylamino)phthalide

HRID 839353Notes

Reaction equation

HRID 839353 reaction equation
[CH3:1][N:2]([CH3:26])[C:3]1[CH:22]=[C:21]([N:23]([CH3:25])[CH3:24])[CH:20]=[CH:19][C:4]=1[C:5]([C:7]1[CH:15]=[C:14]([N:16]([CH3:18])[CH3:17])[CH:13]=[CH:12][C:8]=1[C:9]([OH:11])=[O:10])=O.C(OC(=O)C)(=O)C.[CH3:34][N:35]([CH3:45])[C:36]1[CH:41]=[CH:40][CH:39]=[C:38]([N:42]([CH3:44])[CH3:43])[CH:37]=1>Cl>[CH3:43][N:42]([CH3:44])[C:38]1[CH:37]=[C:36]([N:35]([CH3:45])[CH3:34])[CH:41]=[CH:40][C:39]=1[C:5]1([C:4]2[CH:19]=[CH:20][C:21]([N:23]([CH3:24])[CH3:25])=[CH:22][C:3]=2[N:2]([CH3:26])[CH3:1])[C:7]2[C:8](=[CH:12][CH:13]=[C:14]([N:16]([CH3:17])[CH3:18])[CH:15]=2)[C:9](=[O:10])[O:11]1

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 897151,3-Benzenediamine, N1,N1,N3,N3-tetramethyl-HCID 23343387HCID 23343387, compound

Product 1

HCID 541376933,3-Bis(2,4-bis(dimethylamino)phenyl)-5-(dimethylamino)phthalide

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

A mixture of 2-(2,4-bis(dimethylamino)benzoyl)-4-(dimethylamino)benzoic acid or the 5-(dimethylamino) isomer thereof (10 g.), N,N,N'-tetramethyl-m-phenylenediamine (2.30 g.) and acetic anhydride (50 ml.) was warmed (at 30°-35° C.) during 1 hour. More N,N,N',N'-tetramethyl-m-phenylenediamine (1.15 g.) was added and warming was continued. The mixture was diluted with dilute hydrochloric acid (10%) and ice and filtered. The filtrate was made alkaline. Crystallization of the product from toluene afforded 3,3-bis(2,4-bis(dimethylamino)phenyl)-5-(dimethylamino)phthalide (I: X = Y2 = Y4 = Z5 = (CH3)2N, Z4 = Z6 = Z7 = H) (m.p. 188°-192° C.) or the 6-(dimethylamino) isomer thereof.

Workup

  1. temperaturewarming
  2. filtrationfiltered
  3. customCrystallization of the product from toluene

Sources & evidence

ORD record
ord-fead94beeb1c4f9aa5547d525d45f7bf
Source dataset
uspto-grants-1978_06
Patent number
US04094877

Reaction notes

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