Sodium Hydroxide → HCID 21319288, compound

HRID 262526Notes

Reaction equation

HRID 262526 reaction equation
S(S([O-])=O)([O-])=O.[Na+].[Na+].[N+:9]([C:12]1[CH:13]=[C:14]([CH:19]=[CH:20][C:21]=1[NH2:22])[CH2:15][S:16][CH2:17][CH3:18])([O-])=O.[OH-].[Na+]>O.C(O)C.[OH-].[NH4+]>[NH2:9][C:12]1[CH:13]=[C:14]([CH:19]=[CH:20][C:21]=1[NH2:22])[CH2:15][S:16][CH2:17][CH3:18]

Participants

7

Reactant 3

HCID 14798Sodium HydroxideHCID 24489Sodium Dithionite2×HCID 21319286HCID 21319286, compound

Product 1

HCID 21319288HCID 21319288, compoundYield 92%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolvent2×HCID 14923Ammonium HydroxideSolvent2×

Procedure

A solution of sodium dithionite (2.05 g, 11.8 mmol) dissolved in 20 ml water and 5 ml concentrated ammonium hydroxide is added to the ethyl 3-nitro-4-aminobenzyl sulfide (1 g, 3.9 mmol) stirred in 20 ml 95% ethanol. The mixture is heated to reflux and 0.6 g sodium dithionite in 2 ml water and 0.5 ml ammonium hydroxide is added immediately. The mixture becomes colorless, is cooled to room temperature, basified with 5 ml 10% sodium hydroxide, evaporated to 1/2 volume, and washed with chloroform (X 5). The combined chloroform washings are washed with brine, dried (Na2SO4), and evaporated to give 0.65 g (92%) of an oil which is used without further purification.

Workup

  1. temperatureThe mixture is heated
  2. temperatureto reflux
  3. customevaporated to 1/2 volume
  4. washwashed with chloroform (X 5)
  5. washThe combined chloroform washings are washed with brine
  6. dry with materialdried (Na2SO4)
  7. customevaporated

Sources & evidence

ORD record
ord-8158d9a687b440ef9b6fde7ec83b7a7c
Source dataset
uspto-grants-1979_05
Patent number
US04154846

Reaction notes

Loading…