Phosphorus trichloride → 7-chloro-3-(3,4-dichlorophenyl)-3,4-dihydro-1,9(2H,10H)-acridinedione

HRID 1578083Notes

Reaction equation

HRID 1578083 reaction equation
[Cl:1][C:2]1[CH:15]=[C:14]2[C:5]([N:6](O)[C:7]3[CH2:8][CH:9]([C:18]4[CH:23]=[CH:22][C:21]([Cl:24])=[C:20]([Cl:25])[CH:19]=4)[CH2:10][C:11](=[O:17])[C:12]=3[C:13]2=[O:16])=[CH:4][CH:3]=1.P(Cl)(Cl)Cl>C(Cl)(Cl)Cl>[Cl:1][C:2]1[CH:15]=[C:14]2[C:5]([NH:6][C:7]3[CH2:8][CH:9]([C:18]4[CH:23]=[CH:22][C:21]([Cl:24])=[C:20]([Cl:25])[CH:19]=4)[CH2:10][C:11](=[O:17])[C:12]=3[C:13]2=[O:16])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 24387Phosphorus trichlorideHCID 10250916HCID 10250916, compound

Product 1

HCID 103405087-chloro-3-(3,4-dichlorophenyl)-3,4-dihydro-1,9(2H,10H)-acridinedione

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Conditions

Temperature
50 °C

Procedure

To 3.0 g of 7-chloro-3-(3,4-dichlorophenyl)-3,4-dihydro-10-hydroxy-1,9(2H,10H)-acridinedione suspended in 30 ml of chloroform is added dropwise 2.1 g of phosphorous trichloride in 20 ml of chloroform. The suspension is warmed at 50° C. for 2 hrs and filtered while warm. The solid is suspended in aqueous ethanol and filtered to give 7-chloro-3-(3,4-dichlorophenyl)-3,4-dihydro-1,9(2H,10H)-acridinedione as a cream solid; mp >325° C.

Workup

  1. filtrationfiltered
  2. temperaturewhile warm
  3. filtrationfiltered

Sources & evidence

ORD record
ord-d0959dc2a267441091867f930d2b5754
Source dataset
uspto-grants-1981_09
Patent number
US04291034

Reaction notes

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