Hydrochloric Acid → Thianthrene-2,7-diamine

HRID 905538Notes

Reaction equation

HRID 905538 reaction equation
C([NH:4][C:5]1[CH:18]=[CH:17][C:16]2[S:15][C:14]3[C:9](=[CH:10][CH:11]=[C:12]([NH:19]C(=O)C)[CH:13]=3)[S:8][C:7]=2[CH:6]=1)(=O)C.Cl>C(O)C>[NH2:19][C:12]1[CH:11]=[CH:10][C:9]2[S:8][C:7]3[C:16](=[CH:17][CH:18]=[C:5]([NH2:4])[CH:6]=3)[S:15][C:14]=2[CH:13]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 13215772N,N'-(Thianthrene-2,7-diyl)diacetamide

Product 1

HCID 13215771Thianthrene-2,7-diamineYield 91%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 5.75 g (0.0174 mole) of 2,7-bis(acetylamino)thianthrene, 12 ml of concentrated hydrochloric acid, and 140 ml of ethanol was heated under reflux for 6 hours. The reaction mixture was cooled to room temperature and a precipitate was collected by filtration. The precipitate was added to a mixture of 13.5 ml of concentrated hydrochloric acid and 355 ml of water and the insoluble matters were separated by filtration. The filtered mother liquor was poured into an aqueous solution of sodium hydroxide and the precipitate or 2,7-diaminothianthrene was collected by filtration. The yield was 3.7 g (0.0158 mole, 91% yield) and the purity was 88.2 area % (HPLC, 254 nm).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 6 hours
  3. filtrationa precipitate was collected by filtration
  4. additionThe precipitate was added to a mixture of 13.5 ml of concentrated hydrochloric acid and 355 ml of water
  5. customthe insoluble matters were separated by filtration
  6. additionThe filtered mother liquor was poured into an aqueous solution of sodium hydroxide
  7. filtrationthe precipitate or 2,7-diaminothianthrene was collected by filtration

Sources & evidence

ORD record
ord-789d2a5ebee643329a47c455c184154b
Source dataset
uspto-grants-2011_09
Patent number
US08012606B2

Reaction notes

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