Diethyl Ether → HCID 86747566, compound

HRID 1975245Notes

Reaction equation

HRID 1975245 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([O:9][CH3:10])[C:4]=1[C:11]1[C:24]2[C:15](=[N:16][C:17]3[C:22]([C:23]=2[C:25]([O-:27])=[O:26])=[CH:21][CH:20]=[CH:19][CH:18]=3)[CH:14]=[CH:13][CH:12]=1.[S:28]([F:33])([O:31]C)(=[O:30])=[O:29].CCOCC>ClCCl>[F:33][S:28]([O-:31])(=[O:30])=[O:29].[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([O:9][CH3:10])[C:4]=1[C:11]1[C:24]2[C:15](=[NH+:16][C:17]3[C:22]([C:23]=2[C:25]([OH:27])=[O:26])=[CH:21][CH:20]=[CH:19][CH:18]=3)[CH:14]=[CH:13][CH:12]=1

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 9870Methyl fluorosulfateHCID 19101116HCID 19101116, compound

Product 1

HCID 86747566HCID 86747566, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The compound (2,6-dimethoxy)phenyl-acridine-9-carboxylate (13) (2.01 g, 5.6 mmole) was dissolved in dichloromethane (110 ml, anhydrous) in a 250 ml round bottom flask. Methyl fluorosulfate (4.60 ml, 6.48 g, 56 mmoles) was added and the mixture was stirred at room temperature for 15 hours. Anhydrous ether (100 ml) was added and the precipitated bright yellow solids were filtered after stirring the suspension for 0.5 hours. The solid was washed well with ether (about 100 ml) and then with pentane (50 ml). The acridinium was recrystallized from acetonitrile to provide pure 2,6-dimethoxy-phenyl-acridinium-9-carboxylate fluorosulfonate (14) (yield=81%). The same results may be achieved by crystallization from acetonitrile by the addition of ethyl acetate. Other useful solvent combinations include alcohol and ether, such as methanol, ethanol or propanol and diethyl ether (ether is the precipitating solvent).

Workup

  1. filtrationthe precipitated bright yellow solids were filtered
  2. stirringafter stirring the suspension for 0.5 hours
  3. washThe solid was washed well with ether (about 100 ml)
  4. customThe acridinium was recrystallized from acetonitrile

Sources & evidence

ORD record
ord-05d1076868ab4178b21db48d479bccca
Source dataset
uspto-grants-1994_02
Patent number
US05284952

Reaction notes

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