Tetrachlorophthalic anhydride → HCID 53975483, compound

HRID 1449093Notes

Reaction equation

HRID 1449093 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:20]1[C:28]2[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=2)[CH:22]=[C:21]1[CH3:29])[CH2:17][CH2:18][CH3:19].[Cl-].[Al+3].[Cl-].[Cl-]>C1C=CC=CC=1.Cl>[CH2:16]([N:20]1[C:28]2[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=2)[C:22]([C:11]([C:6]2[C:5]([Cl:13])=[C:4]([Cl:14])[C:3]([Cl:15])=[C:2]([Cl:1])[C:7]=2[C:8]([OH:10])=[O:9])=[O:12])=[C:21]1[CH3:29])[CH2:17][CH2:18][CH3:19]

Participants

6

Reactant 3

HCID 8326Tetrachlorophthalic anhydrideHCID 30848831H-Indole, 1-butyl-2-methyl-HCID 6451240Aluminum(III) Chloride

Product 1

HCID 53975483HCID 53975483, compound

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 313Hydrochloric AcidSolvent

Procedure

Proceeding in a manner similar to that described in part A of Example 2, 14.3 g (0.05 mole) of tetrachlorophthalic anhydride, 16.0 g (0.07 mole) of 76 percent active 1-n-butyl-2-methyindole and 13.3 g (0.10 mole) of aluminum chloride were interacted in 100 ml of benzene. The reaction mixture was drowned in 200 ml of five percent hydrochloric acid with stirring. The solid which formed was collected by filtration, washed with water and dried to obtain 2-[(1-n-butyl-2-methyl3-indolyl)carbonyl]-3,4,5,6-tetrachlorobenzoic acid (Formula VIII: R°=R1 =R2 =R3 =Y1 =H; R5 =CH3 ; R6 =(CH2)3CH3), a pale yellow solid melting at 162°-164° C. The nuclear magnetic resonance spectrum was in accord with the structure.

Workup

  1. customThe solid which formed
  2. filtrationwas collected by filtration
  3. washwashed with water
  4. customdried

Sources & evidence

ORD record
ord-22ca3332c08e4449b5ab9375d4773248
Source dataset
uspto-grants-1980_02
Patent number
US04189171

Reaction notes

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