Aluminum(III) Chloride → 5,6-bis(4-chlorophenyl)pyrimidine-2,4(1H,3H)-dione

HRID 271425Notes

Reaction equation

HRID 271425 reaction equation
C([N:8]1[C:13]([C:14]2[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][CH:15]=2)=[C:12]([C:21]2[CH:26]=[CH:25][C:24]([Cl:27])=[CH:23][CH:22]=2)[C:11](=[O:28])[N:10](CC2C=CC=CC=2)[C:9]1=[O:36])C1C=CC=CC=1.[Al+3].[Cl-].[Cl-].[Cl-]>C1(C)C=CC=CC=1>[Cl:27][C:24]1[CH:23]=[CH:22][C:21]([C:12]2[C:11](=[O:28])[NH:10][C:9](=[O:36])[NH:8][C:13]=2[C:14]2[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][CH:15]=2)=[CH:26][CH:25]=1

Participants

4

Reactant 2

HCID 6451240Aluminum(III) ChlorideHCID 598348061,3-dibenzyl-5,6-bis(4-chlorophenyl)pyrimidine-2,4(1H,3H)-dione

Product 1

HCID 598348265,6-bis(4-chlorophenyl)pyrimidine-2,4(1H,3H)-dioneYield 90%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of 1,3-dibenzyl-5,6-bis(4-chlorophenyl)pyrimidine-2,4(1H,3H)-dione (7.2 g, 14.0 mmol) in toluene (70 mL) was added AlCl3 (4.7 g, 35.2 mmol) under argon. The reaction mixture was stirred in an oil bath preheated at 85° C. for 2 h. The reaction mixture was cooled to room temperature and then poured onto crushed ice (100 g). The precipitate formed was collected by filtration, washed with water (30 mL×2) then ether (40 mL), and dried in a vacuum oven at 40° C. to obtain 4.2 g of the title compound as a brown solid. HPLC/MS (MeOH-water with 10 mM NH4OAc): retention time=3.433 min, [M+H]30 =333.

Workup

  1. additionpoured
  2. customThe precipitate formed
  3. filtrationwas collected by filtration
  4. washwashed with water (30 mL×2)
  5. dry with materialether (40 mL), and dried in a vacuum oven at 40° C.

Sources & evidence

ORD record
ord-d15e0fb472de469e908760088ccff020
Source dataset
uspto-grants-2008_11
Patent number
US07452892B2

Reaction notes

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