Methyl chloroformate → HCID 22117858, compound

HRID 1740461Notes

Reaction equation

HRID 1740461 reaction equation
[H-].[Na+].[CH3:3][C:4]1([CH3:31])[CH2:17][C:16]2[NH:15][C:14]3[CH2:13][C:12]([CH3:19])([CH3:18])[CH2:11][C:10](=[O:20])[C:9]=3[CH:8]([C:21]3[CH:26]=[CH:25][C:24]([N+:27]([O-:29])=[O:28])=[CH:23][CH:22]=3)[C:7]=2[C:6](=[O:30])[CH2:5]1.Cl[C:33]([O:35][CH3:36])=[O:34]>O1CCCC1.CN(C)C=O>[CH3:19][C:12]1([CH3:18])[CH2:13][C:14]2[N:15]([C:33]([O:35][CH3:36])=[O:34])[C:16]3[CH2:17][C:4]([CH3:31])([CH3:3])[CH2:5][C:6](=[O:30])[C:7]=3[CH:8]([C:21]3[CH:26]=[CH:25][C:24]([N+:27]([O-:29])=[O:28])=[CH:23][CH:22]=3)[C:9]=2[C:10](=[O:20])[CH2:11]1

Participants

6

Reactant 3

HCID 6586Methyl chloroformateHCID 24758Sodium hydrideHCID 3763653357-14-0

Product 1

HCID 22117858HCID 22117858, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Procedure

A slurry of 17 mg of sodium hydride (80% dispersion in mineral oil) in 10 ml of anhydrous tetrahydrofuran was stirred at room temperature under an atmosphere of dry nitrogen and treated dropwise with a solution of 200 mg of 3,4,6,7,9,10-hexahydro-3,3,6,6-tetramethyl-9-(4-nitrophenyl)-1,8(2H,5H)-acridinedione in 5 ml of dimethylformamide. The mixture was then heated at reflux for 15 minutes, cooled to room temperature, treated with 44 ml of methyl chloroformate and stirred at room temperature under an atmosphere of dry nitrogen for 18 hours. The solvents were removed under reduced pressure and the resulting waxy residue was taken up in diethyl ether and the insoluble material was filtered off. The filtrate was then purified by column chromatography on silica gel using hexane/ethyl acetate (gradient: 80:20 to 50:50) as the eluent to give methyl 2,3,4,5,6,7,8,9-octahydro-3,3,6,6-tetramethyl-9-(4-nitrophenyl)-1,8-dioxo-1H-acridine-10-carboxylate as a white crystalline solid of melting point 189-190° C.

Workup

  1. temperatureThe mixture was then heated
  2. temperatureat reflux for 15 minutes
  3. customThe solvents were removed under reduced pressure
  4. filtrationthe insoluble material was filtered off
  5. customThe filtrate was then purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-634efefe3a47479fa74a4094c2d5a10c
Source dataset
uspto-grants-1999_10
Patent number
US05969139

Reaction notes

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