Sodium Dithionite → HCID 22749927, compound

HRID 616912Notes

Reaction equation

HRID 616912 reaction equation
[CH2:1]([S:4]([C:6]1[CH:12]=[CH:11][C:9]([NH2:10])=[C:8]([N+:13]([O-])=O)[CH:7]=1)=[O:5])[CH2:2][CH3:3].S(S([O-])=O)([O-])=O.[Na+].[Na+]>C(O)C.O.N>[CH2:1]([S:4]([C:6]1[CH:12]=[CH:11][C:9]([NH2:10])=[C:8]([NH2:13])[CH:7]=1)=[O:5])[CH2:2][CH3:3]

Participants

6

Reactant 2

HCID 24489Sodium DithioniteHCID 203628252-Nitro-4-(propane-1-sulfinyl)aniline

Product 1

HCID 22749927HCID 22749927, compoundYield 60%

Reagents, catalysts & solvents 3

HCID 222AmmoniaSolventHCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a solution of 6.84 g (0.03 mol) of 4-(1-propylsulfinyl)-2-nitroaniline in 100 ml ethanol is added 18.02 g (0.103 mol) sodium hydrosulfite in 100 ml water and 22 mg concentrated aqueous NH3. The resulting solution is heated to reflux for 1 hour, cooled, alcohol stripped and the aqueous layer extracted with CH2Cl2. The organics are combined, dried, filtered and evaporated in vacuo to yield 3.56 g of 4-(1-propylsulfinyl)-1,2-diaminobenzene in the form of an oil, 60% yield.

Workup

  1. temperatureThe resulting solution is heated
  2. temperatureto reflux for 1 hour
  3. temperaturecooled
  4. extractionthe aqueous layer extracted with CH2Cl2
  5. customdried
  6. filtrationfiltered
  7. customevaporated in vacuo

Sources & evidence

ORD record
ord-dd244cf6be3442e78efa5b50c77d507c
Source dataset
uspto-grants-1978_02
Patent number
US04076825

Reaction notes

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