Sodium Sulfite → HCID 58586698, compound

HRID 1393830Notes

Reaction equation

HRID 1393830 reaction equation
Br[CH2:2][CH2:3][NH:4][C:5]1[CH:10]=[CH:9][C:8]([N+:11]([O-:13])=[O:12])=[CH:7][CH:6]=1.[S:14]([O-:17])([O-:16])=[O:15].[Na+:18].[Na+]>C(O)C>[N+:11]([C:8]1[CH:9]=[CH:10][C:5]([NH:4][CH2:3][CH2:2][S:14]([O-:17])(=[O:16])=[O:15])=[CH:6][CH:7]=1)([O-:13])=[O:12].[Na+:18]

Participants

4

Reactant 2

HCID 24437Sodium SulfiteHCID 15868550N-(2-Bromoethyl)-4-nitroaniline

Product 1

HCID 58586698HCID 58586698, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

661 g (2.7 mol) of (2-bromoethyl)(4-nitrophenyl)amine (7) were partially dissolved in 3.7 L of 96% ethanol. At about 75-80° C., aqueous sodium sulfite solution (820 g, 6.5 mol of Na2SO3 in 2.4 L of water) was added. The mixture was stirred at reflux for 11 hours. The resulting mixture was filtered while boiling and the filtrate was allowed to cool. A yellow precipitate formed, which was filtered off by suction and washed with acetone. After drying, 623 g of product were isolated.

Workup

  1. temperatureat reflux for 11 hours
  2. filtrationThe resulting mixture was filtered
  3. temperatureto cool
  4. customA yellow precipitate formed
  5. filtrationwhich was filtered off by suction
  6. washwashed with acetone
  7. customAfter drying

Sources & evidence

ORD record
ord-e51e7e3b96be4c8ea83e1f687932f564
Source dataset
uspto-grants-2008_03
Patent number
US07347879B2

Reaction notes

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