Toluene → 3-(2,4-Bis(dimethylamino)phenyl)-3-(2-acetamido-4-(dimethylamino)phenyl)phthalide

HRID 839536Notes

Reaction equation

HRID 839536 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](O)=[O:10])=[O:6].[CH3:24][N:25]([CH3:36])[C:26]1[CH:27]=[C:28]([CH:33]=[CH:34][CH:35]=1)[NH:29][C:30](=[O:32])[CH3:31].C1(C)C=CC=CC=1>CCCCCC.C(OCC)(=O)C>[CH3:23][N:2]([CH3:1])[C:3]1[CH:19]=[C:18]([N:20]([CH3:21])[CH3:22])[CH:17]=[CH:16][C:4]=1[C:5]1([C:33]2[CH:34]=[CH:35][C:26]([N:25]([CH3:36])[CH3:24])=[CH:27][C:28]=2[NH:29][C:30](=[O:32])[CH3:31])[C:7]2[C:8](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:9](=[O:10])[O:6]1

Participants

6

Reactant 3

HCID 1140TolueneHCID 81988N-(3-(dimethylamino)phenyl)acetamideHCID 202872122-(2,4-Bis(dimethylamino)benzoyl)benzoic acid

Product 1

HCID 233433753-(2,4-Bis(dimethylamino)phenyl)-3-(2-acetamido-4-(dimethylamino)phenyl)phthalide

Reagents, catalysts & solvents 2

HCID 8058HexaneSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

In a manner similar to that of part B of Example 3 condensation of 2-(2,4-bis(dimethylamino)benzoyl)benzoic acid (2.4 g.) and m-(dimethylamino)acetanilide (1.42 g.) and recrystallization of part of the product from a mixture of toluene, ligroin and hexane and part from a mixture of ethyl acetate and hexane afforded 3-(2,4-bis(dimethylamino)phenyl)-3-(2-acetamido-4-(dimethylamino)phenyl)phthalide (I: X = Y4 = (CH3)2N, Y2 = CH3CONH, Z4 = Z5 = Z6 = Z7 = H) (m.p. 97°-136° C.).

Sources & evidence

ORD record
ord-4f0c3b6e45bd48a5af27055e43272438
Source dataset
uspto-grants-1978_06
Patent number
US04096176

Reaction notes

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