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

HRID 1089180Notes

Reaction equation

HRID 1089180 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)(=O)C>CN(C)C=O.[Pd]>[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

5

Reactant 2

HCID 176Acetic AcidHCID 3477103-nitrodibenzothiophene S,S-dioxide

Product 1

HCID 3477115,5-dioxidodibenzo[b,d]thien-3-ylamine

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 6228DimethylformamideSolvent

Procedure

A 10 g portion of 3-nitrodibenzothiophene S,S-dioxide in 180 ml of dimethylformamide and 20 ml of glacial acetic acid containing 1.0 g of 5% palladium on carbon was hydrogenated for 1.75 hours, then filtered through diatomaceous earth and the filtrate evaporated. The residue was dissolved in 250 ml of acetonitrile, filtered through diatomaceous earth and concentrated to 150 ml. The solid was collected, giving 6.95 g of the desired product mp 261°-264° C.

Workup

  1. filtrationfiltered through diatomaceous earth
  2. customthe filtrate evaporated
  3. dissolutionThe residue was dissolved in 250 ml of acetonitrile
  4. filtrationfiltered through diatomaceous earth
  5. concentrationconcentrated to 150 ml
  6. customThe solid was collected

Sources & evidence

ORD record
ord-ef8f4ce33b1048cb90e7ceedb97c4501
Source dataset
uspto-grants-1990_10
Patent number
US04965284

Reaction notes

Loading…