Tetrachlorophthalic anhydride → 2,3,4,5-Tetrachloro-6-[4-(diethylamino)-2-methylbenzoyl]benzoic acid

HRID 839540Notes

Reaction equation

HRID 839540 reaction equation
[Cl:1][C:2]1[C:3]([Cl:15])=[C:4]([Cl:14])[C:5]([Cl:13])=[C:6]2[C:11](=[O:12])[O:10][C:8](=[O:9])[C:7]=12.[CH2:16]([N:18]([CH2:26][CH3:27])[C:19]1[CH:24]=[CH:23][CH:22]=[C:21]([CH3:25])[CH:20]=1)[CH3:17].[Cl-].[Al+3].[Cl-].[Cl-]>ClC1C=CC=CC=1Cl>[CH3:25][C:21]1[CH:20]=[C:19]([N:18]([CH2:16][CH3:17])[CH2:26][CH3:27])[CH:24]=[CH:23][C:22]=1[C:11]([C:6]1[C:5]([Cl:13])=[C:4]([Cl:14])[C:3]([Cl:15])=[C:2]([Cl:1])[C:7]=1[C:8]([OH:10])=[O:9])=[O:12]

Participants

5

Reactant 3

HCID 8326Tetrachlorophthalic anhydrideHCID 66679N,N-diethyl-m-toluidineHCID 6451240Aluminum(III) Chloride

Product 1

HCID 1043362,3,4,5-Tetrachloro-6-[4-(diethylamino)-2-methylbenzoyl]benzoic acidYield 77.3%

Reagents, catalysts & solvents 1

HCID 72391,2-DichlorobenzeneSolvent

Procedure

In a manner similar to that of part A of Example 1 condensation of tetrachlorophthalic anhydride (21.4 g.) and N,N-diethyl-m-toluidine (41 g.) in contact with aluminum chloride (30 g.) and with o-dichlorobenzene (90 ml.) as diluent afforded 2-(2-methyl-4-(diethylamino)benzoyl)-3,4,5,6-tetrachlorobenzoic acid (IV: Y2 = CH3, Y'4 = (CH3CH2)2N, Z4 = Z"5 = Z"6 = Z7 = Cl) (26 g., m.p. 117° C. with sublimation).

Sources & evidence

ORD record
ord-b20524e852264971892ce9841e6c6e56
Source dataset
uspto-grants-1978_06
Patent number
US04096176

Reaction notes

Loading…