Hydrochloric Acid → 5,5-dioxidodibenzo[b,d]thien-3-ylamine

HRID 252435Notes

Reaction equation

HRID 252435 reaction equation
[N+:1]([C:4]1[CH:5]=[CH:6][C:7]2[C:11]3[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=3[S:9](=[O:17])(=[O:16])[C:8]=2[CH:18]=1)([O-])=O.C(O)CC.Cl.[Sn]>O>[NH2:1][C:4]1[CH:5]=[CH:6][C:7]2[C:11]3[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=3[S:9](=[O:17])(=[O:16])[C:8]=2[CH:18]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 10311-PropanolHCID 3477103-nitrodibenzothiophene S,S-dioxideHCID 5352426Tin atom

Product 1

HCID 3477115,5-dioxidodibenzo[b,d]thien-3-ylamineYield 93%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A 3 L round-bottom-flask equipped with a stirring bar, reflux condenser, and gas inlet was charged with 3-nitro-dibenzothiophene-5,5-dioxide (26 g, 0.1 mol), n-propanol (280 mL), water (840 mL), concentrated hydrochloric acid (325 mL), and tin powder, 20 mesh (65 g, 0.55 mol) then purged with nitrogen. The slurry was heated to a reflux overnight, which led to the consumption of the yellow crystals. The hot solution was filtered to remove the remaining tin powder then cooled to room temperature and chilled in an ice bath to crystallize the product. The yellow crystals were collected by vacuum filtration without washing with water then air dried. The crystals were added to a 10% solution of sodium hydroxide (200 mL) to liberate the free amine from the hydrochloride salt. The yellow powder was collected by vacuum filtration, washed well with water, then dried under vacuum to give 21.5 g of 3-amino-dibenzothiophene-5,5-dioxide (93% yield).

Workup

  1. customA 3 L round-bottom-flask equipped with a stirring bar
  2. temperaturereflux condenser, and gas inlet
  3. customthen purged with nitrogen
  4. temperatureThe slurry was heated to a reflux overnight
  5. customwhich led to the consumption of the yellow crystals
  6. filtrationThe hot solution was filtered
  7. customto remove the remaining tin powder
  8. temperaturechilled in an ice bath
  9. customto crystallize the product
  10. filtrationThe yellow crystals were collected by vacuum filtration
  11. washwithout washing with water
  12. customair dried
  13. additionThe crystals were added to a 10% solution of sodium hydroxide (200 mL)
  14. filtrationThe yellow powder was collected by vacuum filtration
  15. washwashed well with water
  16. customdried under vacuum

Sources & evidence

ORD record
ord-36198dd794de4fb1a19e7e1f6cac1065
Source dataset
uspto-grants-2011_01
Patent number
US07868086B2

Reaction notes

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