Hydrochloric Acid → 3,3-Bis(2,4-bis(dimethylamino)phenyl)phthalide

HRID 839535Notes

Reaction equation

HRID 839535 reaction equation
[CH3:1][N:2]([CH3:23])[C:3]1[CH:19]=[C:18]([N:20]([CH3:22])[CH3:21])[CH:17]=[CH:16][C:4]=1[C:5]([C:7]1[CH:15]=[CH:14][CH:13]=[CH:12][C:8]=1[C:9]([OH:11])=O)=[O:6].[CH3:24][N:25]([CH3:35])[C:26]1[CH:31]=[CH:30][CH:29]=[C:28]([N:32]([CH3:34])[CH3:33])[CH:27]=1.C(OC(=O)C)(=O)C.Cl>>[CH3:33][N:32]([CH3:34])[C:28]1[CH:27]=[C:26]([N:25]([CH3:35])[CH3:24])[CH:31]=[CH:30][C:29]=1[C:5]1([C:4]2[CH:16]=[CH:17][C:18]([N:20]([CH3:22])[CH3:21])=[CH:19][C:3]=2[N:2]([CH3:1])[CH3:23])[C:7]2[C:8](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:9](=[O:11])[O:6]1

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 7918Acetic AnhydrideHCID 897151,3-Benzenediamine, N1,N1,N3,N3-tetramethyl-HCID 202872122-(2,4-Bis(dimethylamino)benzoyl)benzoic acid

Product 1

HCID 202165793,3-Bis(2,4-bis(dimethylamino)phenyl)phthalide

Procedure

A mixture of crude 2-(2,4-bis(dimethylamino)benzoyl)benzoic acid (7 g.), N,N,N',N'-tetramethyl-m-phenylenediamine (1.64 g.) and acetic anhydride was warmed (at 25°-35° C.) during 2 to 3 hours, then poured into dilute hydrochloric acid (10%). The resulting mixture was basified and filtered with a filter aid. The filter cake was extracted with hot toluene. Dilution of the toluene extract with hexane afforded 3,3-bis(2,4-bis(dimethylamino)phenyl)phthalide (I: X = Y2 = Y4 = (CH3)2N, Z4 = Z5 = Z6 = Z7 = H) m.p. 186°-188° C.).

Workup

  1. temperaturewas warmed (at 25°-35° C.) during 2 to 3 hours
  2. filtrationfiltered with a filter aid
  3. extractionThe filter cake was extracted with hot toluene
  4. extractionDilution of the toluene extract with hexane

Sources & evidence

ORD record
ord-31f30c2c8304414db010d7917a056a7d
Source dataset
uspto-grants-1978_06
Patent number
US04096176

Reaction notes

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