Triethylamine → HCID 20248125, compound

HRID 1589139Notes

Reaction equation

HRID 1589139 reaction equation
Br[CH2:2][C:3]1[CH:16]=[C:15]([O:17][CH2:18][O:19][CH3:20])[CH:14]=[C:13]2[C:4]=1[N:5]=[C:6]1[C:11](=[N:12]2)[C:10]([O:21][CH2:22][O:23][CH3:24])=[CH:9][CH:8]=[CH:7]1.C(N(CC)CC)C.[Cr](Cl)([O-])(=O)=[O:33].[NH+]1C=CC=CC=1>CS(C)=O.ClCCl.F[B-](F)(F)F.[Ag+]>[CH:2]([C:3]1[CH:16]=[C:15]([O:17][CH2:18][O:19][CH3:20])[CH:14]=[C:13]2[C:4]=1[N:5]=[C:6]1[C:11](=[N:12]2)[C:10]([O:21][CH2:22][O:23][CH3:24])=[CH:9][CH:8]=[CH:7]1)=[O:33]

Participants

7

Reactant 3

HCID 8471TriethylamineHCID 20248124HCID 20248124, compoundHCID 178418287HCID 178418287, compound

Product 1

HCID 20248125HCID 20248125, compoundYield 205%

Reagents, catalysts & solvents 3

HCID 159722Silver tetrafluoroborateCatalystHCID 679Dimethyl SulfoxideSolventHCID 6344DichloromethaneSolvent2×

Procedure

To a solution of silver fluoroborate (359 mg, 1.86 mM) in anhydrous dimethylsulfoxide (15 ml) was added 6-bromomethyl-1,8-di(methoxymethoxy)phenazine (600 mg, 1.53 mM) and the resulting suspension was stirred overnight at room temperature under an argon atmosphere. It was then treated with triethylamine (0.5 ml) and the stirring continued for 30 more minutes. The reaction was diluted with dichloromethane and filtered through Celite. The filtrate was thoroughly washed with water, brine and dried over anhydrous magnesium sulfate. Evaporation under reduced pressure provided yellow solid which was taken up in dry dichloromethane (5 ml) and added to a solution of pyridinium chlorochromate (130 mg, 0.6 mM) in the same solvent (2 ml). After stirring for 3 hours, the reaction was worked up in a standard fashion (ether quench) to give orange solid. Purification by flash chromatography on silica gel (Whatman LPS-1) using chloroform as eluent gave the title compound (406 mg) as yellow needles, melting point 148°-150° C. from chloroform-ether.

Workup

  1. filtrationfiltered through Celite
  2. washThe filtrate was thoroughly washed with water, brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customEvaporation under reduced pressure
  5. customprovided yellow solid which
  6. stirringAfter stirring for 3 hours
  7. customthe reaction was worked up in a standard fashion (ether quench)
  8. customto give orange solid
  9. customPurification by flash chromatography on silica gel (Whatman LPS-1)

Sources & evidence

ORD record
ord-f212bdcdd0384b4eb15a1ee2b2347155
Source dataset
uspto-grants-1986_02
Patent number
US04568675

Reaction notes

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