Sodium Dithionite → HCID 21800091, compound

HRID 1742807Notes

Reaction equation

HRID 1742807 reaction equation
[NH2:1][C:2]1[N:7]([CH2:8][CH:9]2[CH2:11][CH2:10]2)[C:6](=[O:12])[N:5]([CH2:13][CH:14]2[CH2:16][CH2:15]2)[C:4](=[O:17])[C:3]=1[N:18]=O.S(S([O-])=O)([O-])=O.[Na+].[Na+]>O.C(O)C>[NH2:18][C:3]1[C:4](=[O:17])[N:5]([CH2:13][CH:14]2[CH2:15][CH2:16]2)[C:6](=[O:12])[N:7]([CH2:8][CH:9]2[CH2:10][CH2:11]2)[C:2]=1[NH2:1]

Participants

5

Reactant 2

HCID 24489Sodium DithioniteHCID 19071311HCID 19071311, compound

Product 1

HCID 21800091HCID 21800091, compoundYield 84.1%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

Compound c (3.0 g, 11.4 mmol) was suspended in a mixture of 25 ml of water and 40 ml of ethanol. Twenty milliliters of aqueous solution of 6.9 g (40 mmol) of sodium hydrosulfite was added, and the resulting mixture was stirred at room temperature for 2.5 hours. The reaction mixture was extracted three times with 50 ml of chloroform. The organic layer was washed with a saturated aqueous solution of sodium chloride and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by column chromatography (eluent: 3% methanol/chloroform) to give 2.40 g (yield: 84%) of Compound b as an amorphous substance.

Workup

  1. extractionThe reaction mixture was extracted three times with 50 ml of chloroform
  2. washThe organic layer was washed with a saturated aqueous solution of sodium chloride
  3. dry with materialdried over anhydrous sodium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. customthe residue was purified by column chromatography (eluent: 3% methanol/chloroform)

Sources & evidence

ORD record
ord-479394622f634c69896ab63465833078
Source dataset
uspto-grants-1994_08
Patent number
US05342841

Reaction notes

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