2,4-Dichlorobenzoyl chloride → HCID 14371422, compound

HRID 2291983Notes

Reaction equation

HRID 2291983 reaction equation
[C:1]1(=[O:16])[N:5](C2NC=CC=2)[C:4](=[O:11])[C:3]2=[CH:12][CH:13]=[CH:14][CH:15]=[C:2]12.[Cl:17][C:18]1[CH:26]=[C:25]([Cl:27])[CH:24]=[CH:23][C:19]=1[C:20](Cl)=[O:21]>ClC(Cl)C>[Cl:17][C:18]1[CH:26]=[C:25]([Cl:27])[CH:24]=[CH:23][C:19]=1[C:20]([C:4]1[N:5]([N:5]2[C:1](=[O:16])[C:2]3=[CH:15][CH:14]=[CH:13][CH:12]=[C:3]3[C:4]2=[O:11])[CH:1]=[CH:2][CH:3]=1)=[O:21]

Participants

4

Reactant 2

HCID 666452,4-Dichlorobenzoyl chlorideHCID 10536496HCID 10536496, compound

Product 1

HCID 14371422HCID 14371422, compoundYield 16.6%

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Procedure

To a suspension of phthalimidopyrrole (748.6 g) and 2,4-dichlorobenzoyl chloride (1109.1 g) in 3.5 L of dichloroethane was added 707.3 g of K-10 Montmorillonite clay. The resulting mixture was stirred at reflux for 48 hrs, then filtered and concentrated to a semisolid. The semisolid was triturated with a large quantity of ether and collected to yield 112.5 g of powder. The ether wash was concentrated to give 162.0 of a residue. This was purified by high performance liquid chromatography (HPLC hereinafter, silica, dichloromethane) and recrystallized from absolute ethanol to yield 37.26 g of crystals, mp 152°-153° C.

Workup

  1. temperatureat reflux for 48 hrs
  2. filtrationfiltered
  3. concentrationconcentrated to a semisolid
  4. customThe semisolid was triturated with a large quantity of ether
  5. customcollected

Sources & evidence

ORD record
ord-756f8d01a25a4f3aa590e7b5ab821c91
Source dataset
uspto-grants-1989_01
Patent number
US04800203

Reaction notes

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