Triethylamine → 3H-1,4,8b-Triazaacenaphthylene-3,5(4H)-dione

HRID 1068747Notes

Reaction equation

HRID 1068747 reaction equation
NC1C=CC(C[N:9]2[C:19](=[O:20])[C:18]3[N:21]4[C:11](=[CH:12][N:13]=[C:14]4[CH:15]=[CH:16][CH:17]=3)[C:10]2=[O:22])=CC=1.C(N(CC)CC)C.FC(F)(F)S(OS(C(F)(F)F)(=O)=O)(=O)=O>C(Cl)Cl>[N:13]1[CH:12]=[C:11]2[N:21]3[C:18](=[CH:17][CH:16]=[CH:15][C:14]=13)[C:19](=[O:20])[NH:9][C:10]2=[O:22]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 67749Trifluoromethanesulfonic anhydrideHCID 21190076HCID 21190076, compound

Product 1

HCID 211901623H-1,4,8b-Triazaacenaphthylene-3,5(4H)-dione

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a suspension of 1.46 g (5.0 mmol) of 4-[4-(amino)phenylmethyl]-4,5-dihydro-3H-1,4,8b-triazaacenaphthylene-3,5-dione and 1.05 ml (7.5 mmol) of triethylamine in methylene chloride (100 ml) was added dropwise, while stirring under ice-cooling, 1.01 ml (6.0 mmol) of trifluoromethanesulfonic acid anhydride. The mixture was stirred for one hour at room temperature. The reaction mixture was washed with 1N-HCl, and dried over anhydrous magnesium sulfate. The solvent was distilled off, and the residue was eluted by column chromatography (eluent:chloroform/ethyl acetate=1:1) to afford 502 mg of 4,5-dihydro-4-[4-bis(trifluoromethane sulfonyl)imido)phenylmethyl]-3H-1,4,8b-triazaacenaphthylene-3,5-dione (18.1%, a pale reddish brown solid).

Workup

  1. additionwas added dropwise
  2. temperaturecooling
  3. stirringThe mixture was stirred for one hour at room temperature
  4. washThe reaction mixture was washed with 1N-HCl
  5. dry with materialdried over anhydrous magnesium sulfate
  6. distillationThe solvent was distilled off
  7. washthe residue was eluted by column chromatography (eluent:chloroform/ethyl acetate=1:1)

Sources & evidence

ORD record
ord-a2b9f5b535d94c4f83b4063e014f6144
Source dataset
uspto-grants-2001_06
Patent number
US06251905B1

Reaction notes

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