Tetrachlorophthalic anhydride → HCID 53975483, compound

HRID 1660278Notes

Reaction equation

HRID 1660278 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-methylindole 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-methyl-3-indolyl)carbonyl]-3,4,5,6-tetrachlorobenzoic acid (Formula VIII: Ro =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-164382a2df7440bebf922371d64ccf5e
Source dataset
uspto-grants-1981_12
Patent number
US04307018

Reaction notes

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