Water → HCID 68156219, compound

HRID 1627751Notes

Reaction equation

HRID 1627751 reaction equation
[C:1]1([C:7]2([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)[C:20]3[C:15]4=[C:16]([C:21]5[CH:22]=[CH:23][CH:24]=[CH:25][C:26]=5[N:14]4[C:13]4[CH:12]=[CH:11][CH:10]=[CH:9][C:8]2=4)[CH:17]=[CH:18][CH:19]=3)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Al+3].[Cl-].[Cl-].[Cl-].[C:37](Cl)(=[O:44])[C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1.O>C(Cl)(Cl)Cl>[C:27]1([C:7]2([C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)[C:20]3[C:15]4=[C:16]([C:21]5[CH:22]=[C:23]([C:37]([C:38]6[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=6)=[O:44])[CH:24]=[CH:25][C:26]=5[N:14]4[C:13]4[CH:12]=[CH:11][CH:10]=[CH:9][C:8]2=4)[CH:17]=[CH:18][CH:19]=3)[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7412Benzoyl chlorideHCID 6451240Aluminum(III) ChlorideHCID 59235958HCID 59235958, compound

Product 1

HCID 68156219HCID 68156219, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A degassed solution of 6.1 g (18 mmol) of 8,8-diphenyl-8H-indolo-[3,2,1-de]acridine in 40 ml of chloroform is cooled to 0° C., and 5 g (37 mmol) of AlCl3 are added. 3.9 g of benzoyl chloride are then added dropwise at this temperature, and the mixture is stirred for 8 h. 50 ml of water are added to the mixture, and the organic phase is separated off, filtered through silica gel and evaporated to dryness. The residue is recrystallised from toluene and from dichloromethane/isopropanol and finally sublimed in a high vacuum, the purity is 99.9%. The yield is 13.7 g (27 mmol), corresponding to 90% of theory.

Workup

  1. customthe organic phase is separated off
  2. filtrationfiltered through silica gel
  3. customevaporated to dryness
  4. customThe residue is recrystallised from toluene and from dichloromethane/isopropanol

Sources & evidence

ORD record
ord-2f09f24d7eb443a4b6ce4fed1b81bce7
Source dataset
uspto-grants-2014_07
Patent number
US08785636B2

Reaction notes

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