Water → HCID 21938259, compound

HRID 1242137Notes

Reaction equation

HRID 1242137 reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].[Cl:5][C:6]1[CH:14]=[C:13]([Cl:15])[CH:12]=[CH:11][C:7]=1[C:8](Cl)=[O:9].[CH3:16][O:17][C:18]([C:20]1[CH:21]=[C:22]2[C:26](=[CH:27][CH:28]=1)[NH:25][C:24]([CH3:29])=[CH:23]2)=[O:19].O>C(Cl)Cl>[Cl:5][C:6]1[CH:14]=[C:13]([Cl:15])[CH:12]=[CH:11][C:7]=1[C:8]([C:23]1[C:22]2[C:26](=[CH:27][CH:28]=[C:20]([C:18]([O:17][CH3:16])=[O:19])[CH:21]=2)[NH:25][C:24]=1[CH3:29])=[O:9]

Participants

6

Reactant 4

HCID 962WaterHCID 666452,4-Dichlorobenzoyl chlorideHCID 6451240Aluminum(III) ChlorideHCID 12230324HCID 12230324, compound

Product 1

HCID 21938259HCID 21938259, compoundYield 62.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Aluminium chloride (0.86 g) is suspended in methylene chloride (30 ml), to which are added 2,4-dichlorobenzoyl chloride (0.67 g) and then 5-(methoxycarbonyl)-2-methylindole (0.50 g) and stirred at 50° C. for 3 hours and then at room temperature for 41 hours. The reaction mixture is poured into water with ice, and extracted twice with ethyl acetate. The organic layer is washed twice with a saturated aqueous sodium hydrogencarbonate solution and then with a saturated saline solution, and thereafter dried with anhydrous sodium sulfate. The drying agent is removed through filtration, and the filtrate is concentrated under reduced pressure. The resulting crystal is washed with t-butyl methyl ether, and dried to obtain a crystal of 3-(2,4-dichlorobenzoyl)-5-(methoxycarbonyl)-2-methylindole (61) (0.60 g).

Workup

  1. extractionextracted twice with ethyl acetate
  2. washThe organic layer is washed twice with a saturated aqueous sodium hydrogencarbonate solution
  3. dry with materialwith a saturated saline solution, and thereafter dried with anhydrous sodium sulfate
  4. customThe drying agent is removed through filtration
  5. concentrationthe filtrate is concentrated under reduced pressure
  6. washThe resulting crystal is washed with t-butyl methyl ether
  7. customdried

Sources & evidence

ORD record
ord-54564f8969f74076aa7b2fe3078769d9
Source dataset
uspto-grants-2006_10
Patent number
US07115647B2

Reaction notes

Loading…