1-Bromo-7-nitro-thianthrene → 6-Bromo-thianthren-2-ylamine

HRID 33791Notes

Reaction equation

HRID 33791 reaction equation
[Br:1][C:2]1[C:15]2[S:14][C:13]3[C:8](=[CH:9][C:10]([N+:16]([O-])=O)=[CH:11][CH:12]=3)[S:7][C:6]=2[CH:5]=[CH:4][CH:3]=1>C(O)(=O)C.[Zn]>[Br:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:15]=1[S:14][C:13]1[CH:12]=[CH:11][C:10]([NH2:16])=[CH:9][C:8]=1[S:7]2

Participants

4

Reactant 1

HCID 597974311-Bromo-7-nitro-thianthrene

Product 1

HCID 597974306-Bromo-thianthren-2-ylamineYield 104%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 176Acetic AcidSolvent

Procedure

Zn dust (144.1 g, 2.2 mol) was added to a stirred solution of 1-bromo-7-nitro-thianthrene (125 g, 367.4 mmol) in glacial acetic acid (500 ml at 0° C. (ice bath). After one hour the ice bath was removed and the solution was left to react overnight at room temperature. The mixture was filtered through a pad of Celite and washed with copious amount of dichloromethane and the filtrate was evaporated in vacuo. Water was added (500 ml) to the residue and the pH was adjusted to pH 8 by addition of concentrated ammonia. The solid formed was filtered and dried in a vacuum desiccator to give the title compound (118.5 g) and was used without any further purification. m/z (LC-MS, ESP), RT=4.92, (M++1)=310-312 (1:1, bromine isotope ratio present)

Workup

  1. customAfter one hour the ice bath was removed
  2. waitthe solution was left
  3. customto react overnight at room temperature
  4. filtrationThe mixture was filtered through a pad of Celite
  5. washwashed with copious amount of dichloromethane
  6. customthe filtrate was evaporated in vacuo
  7. additionWater was added (500 ml) to the residue
  8. additionthe pH was adjusted to pH 8 by addition of concentrated ammonia
  9. customThe solid formed
  10. filtrationwas filtered
  11. customdried in a vacuum desiccator

Sources & evidence

ORD record
ord-8ef930c0e2344088b06312cac3797f1e
Source dataset
uspto-grants-2008_09
Patent number
US07429660B2

Reaction notes

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