Dibenzothiophene, 3,7-dinitro-, 5-oxide → Dibenzo[b,d]thiophene-3,7-diamine

HRID 71865Notes

Reaction equation

HRID 71865 reaction equation
[N+:1]([C:4]1[CH:5]=[CH:6][C:7]2[C:11]3[CH:12]=[CH:13][C:14]([N+:16]([O-])=O)=[CH:15][C:10]=3[S:9](=O)[C:8]=2[CH:20]=1)([O-])=O>C(O)C.[Pd]>[CH:12]1[C:11]2[C:7]3[CH:6]=[CH:5][C:4]([NH2:1])=[CH:20][C:8]=3[S:9][C:10]=2[CH:15]=[C:14]([NH2:16])[CH:13]=1

Participants

4

Reactant 1

HCID 15487214Dibenzothiophene, 3,7-dinitro-, 5-oxide

Product 1

HCID 9990823Dibenzo[b,d]thiophene-3,7-diamine

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

Two batches of the above solid 3,7-dinitro-dibenzothiophene 5-oxide was hydrogenated at 45 psi in ethanol (250 mL for each batch) with 10% Pd on carbon (0.46 g each batch) for 2 hours. Two batches were combined and filtered through CELITE to give an orange solution. Hydrogen chloride gas was bubbled into the solution to form precipitate (at pH 1). The precipitate was filtered and washed with small amount of ethanol and dried on vacuum to give an orange solid Dibenzothiophene-3,7-diamine (2.46 g). LCMS-ESI−: calc'd for C12H10N2S: 214.29. Found: 215.0 (M+H+).

Workup

  1. customfor 2 hours
  2. filtrationfiltered through CELITE
  3. customto give an orange solution
  4. customHydrogen chloride gas was bubbled into the solution to form precipitate (at pH 1)
  5. filtrationThe precipitate was filtered
  6. washwashed with small amount of ethanol
  7. customdried on vacuum

Sources & evidence

ORD record
ord-53900543bb004ea8a9b8964f721e2c9f
Source dataset
uspto-grants-2014_09
Patent number
US08822430B2

Reaction notes

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