Hydrazine → Thianthrene-2,7-diamine

HRID 1442466Notes

Reaction equation

HRID 1442466 reaction equation
[N+:1]([C:4]1[CH:17]=[CH:16][C:15]2[S:14][C:13]3[C:8](=[CH:9][CH:10]=[C:11]([N+:18]([O-])=O)[CH:12]=3)[S:7][C:6]=2[CH:5]=1)([O-])=O.NN>C(O)C>[NH2:18][C:11]1[CH:10]=[CH:9][C:8]2[S:7][C:6]3[C:15](=[CH:16][CH:17]=[C:4]([NH2:1])[CH:5]=3)[S:14][C:13]=2[CH:12]=1

Participants

4

Reactant 2

HCID 9321HydrazineHCID 43965782,7-dinitrothianthrene

Product 1

HCID 13215771Thianthrene-2,7-diamine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 2,7-dinitrothianthrene (550 mg, 1.8 mmole) in 100 mL of ethanol was added graphite (1.72 g, 144 mmole) and hydrazine (0.56 mL, 18 mmole) with continued stirring and the mixture was refluxed for over night. The reaction mixture was cooled to room temperature and filter through a short column of celite 545. The solvent was then removed and the resulting white solid was dried in vacuo. It was then recrystallized from CHCl3 or used without further purification. mp 185˜186° C. 1H NMR (300 MHz, CDCl3) δ: 7.15 (d, 2H, J=8.1 Hz), 6.81 (d, 2H, J=2.7 Hz), 6.52 (dd, 2H, J=8.1, 2.7 Hz), 3.68 (bs, 4H). 13C NMR (75 MHz, d6-acetone) δ: 149.5, 139.1, 130.0, 121.9, 114.8, 114.6. HR-MS (ESI): calcd. for C12H10N2S2+Na 269.0178 [(M+Na)+]. Found 269.0176.

Workup

  1. temperaturethe mixture was refluxed for over night
  2. filtrationfilter through a short column of celite 545
  3. customThe solvent was then removed
  4. customthe resulting white solid was dried in vacuo
  5. customIt was then recrystallized from CHCl3
  6. customused without further purification

Sources & evidence

ORD record
ord-97e261814a4c46b18ef8f5259f789e8e
Source dataset
uspto-grants-2010_02
Patent number
US07658868B2

Reaction notes

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