Nitric Acid → HCID 15132458, compound

HRID 1089181Notes

Reaction equation

HRID 1089181 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]2[C:9]3[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=3[S:7](=[O:15])(=[O:14])[C:6]=2[CH:16]=1.[N+:17]([O-])([OH:19])=[O:18]>S(=O)(=O)(O)O>[F:1][C:2]1[CH:3]=[CH:4][C:5]2[C:9]3[CH:10]=[CH:11][C:12]([N+:17]([O-:19])=[O:18])=[CH:13][C:8]=3[S:7](=[O:15])(=[O:14])[C:6]=2[CH:16]=1

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 15132457HCID 15132457, compound

Product 1

HCID 15132458HCID 15132458, compoundYield 70.9%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Conditions

Temperature
18 °C

Procedure

To a mixture of 8.94 g of 3-fluorodibenzothiophene S,S-dioxide in 100 ml of concentrated sulfuric acid, cooled at 18° C. in a water bath, was added dropwise 3.12 g of 71% nitric acid over 3 minutes. The mixture was stirred at room temperature for one hour, then poured over 500 ml of crushed ice and the solid collected, washed with water until neutral then dried at 100° C. This solid was dissolved in 200 ml of acetonitrile, treated with charcoal, filtered through diatomaceous earth and the filtrate concentrated to 110 ml producing successive crops of crystals. The first two crops were combined and recrystallized from 100 ml of acetonitrile, giving 7.56 g of the desired product as a solid, mp 275°-279° C.

Workup

  1. customthe solid collected
  2. washwashed with water until neutral
  3. customthen dried at 100° C
  4. dissolutionThis solid was dissolved in 200 ml of acetonitrile
  5. additiontreated with charcoal
  6. filtrationfiltered through diatomaceous earth
  7. concentrationthe filtrate concentrated to 110 ml
  8. customproducing successive crops of crystals
  9. customrecrystallized from 100 ml of acetonitrile

Sources & evidence

ORD record
ord-82ea79b7359144ba8dc48b1ec6e67ea9
Source dataset
uspto-grants-1990_10
Patent number
US04965284

Reaction notes

Loading…