Tetrachlorophthalic anhydride → 2-(2-Isobutoxy-4-(dimethylamino)benzoyl)benzoic acid

HRID 839542Notes

Reaction equation

HRID 839542 reaction equation
Cl[C:2]1[C:3](Cl)=[C:4](Cl)[C:5](Cl)=[C:6]2[C:11](=[O:12])[O:10][C:8](=[O:9])[C:7]=12.CN(C)[C:18]1[CH:23]=[CH:22][CH:21]=[C:20]([N:24]([CH3:26])[CH3:25])[CH:19]=1>[Cl-].[Zn+2].[Cl-].ClC1C=CC=CC=1>[CH2:8]([O:9][C:18]1[CH:19]=[C:20]([N:24]([CH3:26])[CH3:25])[CH:21]=[CH:22][C:23]=1[C:8]([C:7]1[CH:2]=[CH:3][CH:4]=[CH:5][C:6]=1[C:11]([OH:10])=[O:12])=[O:9])[CH:7]([CH3:6])[CH3:2]

Participants

5

Reactant 2

HCID 8326Tetrachlorophthalic anhydrideHCID 897151,3-Benzenediamine, N1,N1,N3,N3-tetramethyl-

Product 1

HCID 233433772-(2-Isobutoxy-4-(dimethylamino)benzoyl)benzoic acid

Reagents, catalysts & solvents 2

HCID 3007855ZincchlorideCatalystHCID 7964ChlorobenzeneSolvent

Procedure

In a manner similar to that of part A of Example 3 condensation of tetrachlorophthalic anhydride (1.92 g.) and N,N,N',N'-tetramethyl-m-phenylenediamine (1.64 g.) in contact with zinc chloride (1.35 g.) and with chlorobenzene (40-45 ml.) as diluent afforded 2-(2,4-bis(dimethylamino)benzoyl)-3,4,5,6-tetrachlorobenzoic acid (II: Y'2 = Y'4 = (CH3)2N, Z4 = Z'5 = Z'6 = Z7 = Cl) (m.p. 199°-201° C.).

Sources & evidence

ORD record
ord-00fc089ed7494f2fa6adce3dc56ffa53
Source dataset
uspto-grants-1978_06
Patent number
US04096176

Reaction notes

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