Benzoic Acid → 3-(2,4-Bis(diethylamino)phenyl)-3-(4-(dimethylamino)phenyl)phthalide

HRID 27022Notes

Reaction equation

HRID 27022 reaction equation
C(O)(=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:10]([N:12]([CH2:24][CH3:25])[C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([N:19]([CH2:22][CH3:23])[CH2:20][CH3:21])[CH:14]=1)[CH3:11].[C:26]([O:29][C:30](=[O:32])[CH3:31])(=O)[CH3:27]>CO>[CH2:20]([N:19]([CH2:22][CH3:23])[C:15]1[CH:14]=[C:13]([N:12]([CH2:10][CH3:11])[CH2:24][CH3:25])[CH:18]=[CH:17][C:16]=1[C:26]1([C:5]2[CH:4]=[CH:3][C:2]([N:12]([CH3:13])[CH3:10])=[CH:7][CH:6]=2)[C:27]2[C:31](=[CH:14][CH:15]=[CH:16][CH:17]=2)[C:30](=[O:32])[O:29]1)[CH3:21]

Participants

5

Reactant 3

HCID 243Benzoic AcidHCID 7918Acetic AnhydrideHCID 19382815N~1~,N~1~,N~3~,N~3~-Tetraethylbenzene-1,3-diamine

Product 1

HCID 538941733-(2,4-Bis(diethylamino)phenyl)-3-(4-(dimethylamino)phenyl)phthalide

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
52 °C

Procedure

A mixture of 2-(4-dimethylamino)benzoyl)benzoic acid (8.07 g.), N,N,N',N'-tetraethyl-m-phenylenediamine (7.26 g.) and acetic anhydride (5 ml.) was heated (at 52° C.) during one and one-half hours. Addition of methanol (10 ml., then 15 ml.) afforded 3-(2,4-bis(diethylamino)phenyl)-3-(4-(dimethylamino)phenyl)phthalide (I: X=(CH3CH2)2N, Y2 =Z4 =Z5 =Z6 =Z7 =H, Y4 =(CH3)2N) (10.92 g., m.p. 117°-119° C.).

Sources & evidence

ORD record
ord-f30f47db2f8442358566541d361949ef
Source dataset
uspto-grants-1980_09
Patent number
US04220357

Reaction notes

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