Réaction #595302

ord-42cb651e0bc74da2887d168130354288

Équation de réaction

Cn1c(=O)c2sc3c(=O)n(C)c(=O)c3sc2c1=O
2,6-dimethyl-1H,5H-[1,4]dithiino[2,3-c:5,6-c′]dipyrrole-1,3,5,7(2H,6H)-tetrone
O=[N+]([O-])O
nitric acid
→
CN1C(=O)C2=C(C1=O)S(=O)C1=C(S2)C(=O)N(C)C1=O
2,6-dimethyl-1H,5H-[1,4]dithiino[2,3-c:5,6-c′]dipyrrole-1,3,5,7(2H,6H)-tetrone 4-oxide

Réactifs

Cn1c(=O)c2sc3c(=O)n(C)c(=O)c3sc2c1=O
2,6-dimethyl-1H,5H-[1,4]dithiino[2,3-c:5,6-c′]dipyrrole-1,3,5,7(2H,6H)-tetrone
O=[N+]([O-])O
nitric acid
—
ice water

Réactifs

Aucun

Solvants

—
ice

Conditions de réaction

Température
5°CELSIUS
Conditions détaillées
See reaction.notes.procedure_details.

Traitement

  1. 1
    workup.DISSOLUTIONAfter dissolution
  2. 2
    workup.STIRRINGstirring
  3. 3
    Filtrationthe yellow crystals were filtered off with suction

Mode opératoire

With stirring, 3 g (10.63 mmol) of 2,6-dimethyl-1H,5H-[1,4]dithiino[2,3-c:5,6-c′]dipyrrole-1,3,5,7(2H,6H)-tetrone [compound No. (1)] were added to 20 ml of ice-cooled (5° C.) fuming nitric acid. After dissolution was complete, stirring was continued for 5 min, the mixture was subsequently poured into ice-water and the yellow crystals were filtered off with suction. This gave 2.56 g (80.8% of theory) of the desired compound.

Source

DOI: 10.6084/m9.figshare.5104873.v1Brevet: US09095140B2uspto-grants-2015_08