5-Bromo-2-nitro-9H-thioxanthene → HCID 59797442, compound

HRID 33806Notes

Reaction equation

HRID 33806 reaction equation
[Br:1][C:2]1[CH:15]=[CH:14][CH:13]=[C:12]2[C:3]=1[S:4][C:5]1[CH:6]=[CH:7][C:8]([N+:16]([O-])=O)=[CH:9][C:10]=1[CH2:11]2>C(O)(=O)C.[Zn]>[Br:1][C:2]1[CH:15]=[CH:14][CH:13]=[C:12]2[C:3]=1[S:4][C:5]1[CH:6]=[CH:7][C:8]([NH2:16])=[CH:9][C:10]=1[CH2:11]2

Participants

4

Reactant 1

HCID 597974365-Bromo-2-nitro-9H-thioxanthene

Product 1

HCID 59797442HCID 59797442, compoundYield 102.6%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 176Acetic AcidSolvent

Procedure

Zn dust (34.87 g, 533 mmol) was added to a stirred solution of 5-bromo-2-nitro-9H-thioxanthene (28.64 g, 88.9 mmol) in glacial acetic acid (300 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 (800 ml) to the residue and the pH was adjusted to pH 8 by addition of concentrated ammonia (100 ml). The solid formed was filtered and dried in a vacuum desiccator to give the title compound (26.64 g) and was used without any further purification. m/z (LC-MS, ESP), RT=4.53 min, (M++1)=294-292, (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 (800 ml) to the residue
  8. additionthe pH was adjusted to pH 8 by addition of concentrated ammonia (100 ml)
  9. customThe solid formed
  10. filtrationwas filtered
  11. customdried in a vacuum desiccator

Sources & evidence

ORD record
ord-1b0d4fc123124ec2b947b4794a33e6ac
Source dataset
uspto-grants-2008_09
Patent number
US07429660B2

Reaction notes

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