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

HRID 27026

Reaction equation

HRID 27026 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]([CH2:25][CH3:26])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[CH3:17].[Cl-].[Al+3].[Cl-].[Cl-].Cl[C:32]1C=CC=CC=1>>[CH3:32][C:23]1[CH:24]=[C:19]([N:18]([CH2:16][CH3:17])[CH2:25][CH3:26])[CH:20]=[CH:21][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 4

HCID 7061N,N-DiethylanilineHCID 7964ChlorobenzeneHCID 8326Tetrachlorophthalic anhydrideHCID 6451240Aluminum(III) Chloride

Product 1

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

Conditions

Temperature
75 °C

Procedure

A mixture of tetrachlorophthalic anhydride (42.8 g.), N,N-diethylaniline (74 g.), aluminum chloride (60 g.) and chlorobenzene (180 ml.) was heated (to 75° C.) during one and one-half hours, then diluted with ice-water (500 ml.). The chlorobenzene layer was separated and steam distilled. Addition of sodium hydroxide solution (50%) to a solution of the residue in dilute sulfuric acid (50%, 250 ml.) afforded 2-(4-(diethylamino)benzoyl)-3,4,5,6-tetrachlorobenzoic acid (IV: Y2 =H, Y'4 =(CH3CH2)2N, Z4 =Z"5 =Z"6 =Z7 =Cl) (59 g., m.p. 228°-233° C.).

Workup

  1. customThe chlorobenzene layer was separated
  2. distillationsteam distilled
  3. additionAddition of sodium hydroxide solution (50%) to a solution of the residue in dilute sulfuric acid (50%, 250 ml.)

Sources & evidence

ORD record
ord-424e1e70aecd4d2ca88393f18c905379
Source dataset
uspto-grants-1980_09
Patent number
US04220357

Linked notes

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