Nitric Acid → Thianthrene, 5-oxide

HRID 1982751Notes

Reaction equation

HRID 1982751 reaction equation
[CH:1]1[C:14]2[S:13][C:12]3[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=3)[S:6][C:5]=2[CH:4]=[CH:3][CH:2]=1.[N+]([O-])(O)=[O:16]>C(O)(=O)C.O>[CH:11]1[C:12]2[S:13][C:14]3[C:5](=[CH:4][CH:3]=[CH:2][CH:1]=3)[S:6](=[O:16])[C:7]=2[CH:8]=[CH:9][CH:10]=1

Participants

5

Reactant 2

HCID 944Nitric AcidHCID 7109Thianthrene

Product 1

HCID 73220Thianthrene, 5-oxide

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

Thianthrene (20 g) was refluxed in 300 ml of acetic acid, and 36 ml of dilute nitric acid was gradually added dropwise thereto. After allowing the reaction to proceed for 5 hours, the reaction solution obtained was poured in 1.2 liter of water to precipitate a crystal. The crystal was collected by filtration and then recrystallized from acetonitrile to obtain 12 g of thianthrene-S-oxide. 1H-NMR (400 MHz, CDCl3): δ 7.42 (t, 2H), 7.56 (t, 2H), 7.63 (d, 2H), 7.93 (d, 2H).

Workup

  1. customthe reaction
  2. customthe reaction solution obtained
  3. customto precipitate a crystal
  4. filtrationThe crystal was collected by filtration
  5. customrecrystallized from acetonitrile

Sources & evidence

ORD record
ord-16b8ab106e5d4b21bac8b71bbb71805e
Source dataset
uspto-grants-2009_06
Patent number
US07541131B2

Reaction notes

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