Nitric Acid → 3-nitrodibenzothiophene S,S-dioxide

HRID 1089179Notes

Reaction equation

HRID 1089179 reaction equation
[CH:1]1[CH:6]=[C:5]2[C:7]3[C:12]([S:13](=[O:15])(=[O:14])[C:4]2=[CH:3][CH:2]=1)=[CH:11][CH:10]=[CH:9][CH:8]=3.[N+:16]([O-])([OH:18])=[O:17]>S(=O)(=O)(O)O>[N+:16]([C:2]1[CH:1]=[CH:6][C:5]2[C:7]3[CH:8]=[CH:9][CH:10]=[CH:11][C:12]=3[S:13](=[O:15])(=[O:14])[C:4]=2[CH:3]=1)([O-:18])=[O:17]

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 13908Dibenzothiophene 5,5-dioxide

Product 1

HCID 3477103-nitrodibenzothiophene S,S-dioxideYield 84.5%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

To a solution of 43.25 g of dibenzothiophene sulfone in 400 ml of concentrated sulfuric acid, cooled in an ice/salt bath, was added dropwise at 0° to 2° C., 17.0 g of 71% nitric acid over 16 minutes. This mixture was stirred at 0° to -10° C. for 30 minutes and then poured over 2 liters of crushed ice. The solid was collected, washed with water until neutral and dried. This solid was dissolved in 750 ml giving three successive crops of precipitate. These crops were combined, giving 44.14 g of the desired product as a solid, mp 260°-267° C.

Workup

  1. additionwas added dropwise at 0° to 2° C.
  2. customThe solid was collected
  3. washwashed with water until neutral and
  4. customdried
  5. dissolutionThis solid was dissolved in 750 ml
  6. customgiving three successive crops of precipitate

Sources & evidence

ORD record
ord-4762f305ccd7443ca73f2abb9b924fb0
Source dataset
uspto-grants-1990_10
Patent number
US04965284

Reaction notes

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