Acetic Acid → 3-nitrodibenzothiophene S,S-dioxide

HRID 252434Notes

Reaction equation

HRID 252434 reaction equation
C(O)(=O)C.S(=O)(=O)(O)O.[CH:10]1[C:18]2[C:17]3[CH:19]=[CH:20][CH:21]=[CH:22][C:16]=3[S:15](=[O:24])(=[O:23])[C:14]=2[CH:13]=[CH:12][CH:11]=1.[N+:25]([O-])([OH:27])=[O:26]>O>[N+:25]([C:21]1[CH:20]=[CH:19][C:17]2[C:18]3[CH:10]=[CH:11][CH:12]=[CH:13][C:14]=3[S:15](=[O:24])(=[O:23])[C:16]=2[CH:22]=1)([O-:27])=[O:26]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 944Nitric AcidHCID 1118Sulfuric AcidHCID 13908Dibenzothiophene 5,5-dioxide

Product 1

HCID 3477103-nitrodibenzothiophene S,S-dioxideYield 85%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A 1 L three-neck round-bottom flask equipped with an addition funnel, mechanical stirrer, and thermocouple was charged with glacial acetic acid (110 mL) and sulfuric acid (110 mL) under nitrogen followed by dibenzothiophene-5,5-dioxide (50 g, 0.231 mol). The slurry was stirred and cooled to below 0° C. Fuming nitric acid, 90% (118 mL, 2.5 mol; specific gravity 1.5) was added dropwise over a period of 1.5 hours to keep the temperature below 4° C. The slurry was stirred for 30 minutes then poured onto 1.5 kg ice rinsing the flask with water. The product was collected by vacuum filtration, washed with water several times, and air dried followed by drying in a vacuum oven. The product was recrystallized from acetonitrile to give 51 g yellow crystals of 3-nitro-dibenzothiophene-5,5-dioxide (85% yield).

Workup

  1. customA 1 L three-neck round-bottom flask equipped with an addition funnel, mechanical stirrer
  2. temperaturecooled to below 0° C
  3. customthe temperature below 4° C
  4. stirringThe slurry was stirred for 30 minutes
  5. filtrationThe product was collected by vacuum filtration
  6. washwashed with water several times, and air
  7. customdried
  8. customby drying in a vacuum oven
  9. customThe product was recrystallized from acetonitrile

Sources & evidence

ORD record
ord-1b3843e61f5f4f48a2adca869625b3a8
Source dataset
uspto-grants-2011_01
Patent number
US07868086B2

Reaction notes

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