Hydrochloric Acid → 5-Nitro-2-thenoic acid

HRID 1956461Notes

Reaction equation

HRID 1956461 reaction equation
[N+:1]([C:4]1[S:8][C:7]([CH:9]=[O:10])=[CH:6][CH:5]=1)([O-:3])=[O:2].OO.[O-:13]Cl=O.[Na+].S([O-])([O-])=O.[Na+].[Na+].Cl>C(#N)C.O>[N+:1]([C:4]1[S:8][C:7]([C:9]([OH:13])=[O:10])=[CH:6][CH:5]=1)([O-:3])=[O:2]

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 784Hydrogen PeroxideHCID 24437Sodium SulfiteHCID 782815-Nitrothiophene-2-carboxaldehydeHCID 23668197Sodium Chlorite

Product 1

HCID 805915-Nitro-2-thenoic acid

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

To a cold (0° C.) mixture of 5-nitro-thiophene-2-carboxaldehyde (10-1) (7.86 g, 50 mmol), NaH2PO4 (1.86 g, dissolved in 20 mL water), 30% H2O2 (6 mL) in acetonitrile (50 mL), a solution of NaClO2 (8 g) in water (70 mL) was added over a period of 1 h. After stirring at RT for 5 h, the reaction mixture was treated with sodium sulfite (500 mg) and 1M aq. HCl. The resultant mixture was extracted with ethyl acetate (3×). The organic extracts were combined, washed with brine, dried over anhdrous magnesium sulfate, filtered, and concentrated under vacuum to provide acid 10-2.

Workup

  1. extractionThe resultant mixture was extracted with ethyl acetate (3×)
  2. washwashed with brine
  3. dry with materialdried over anhdrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-a546a6eaf94844d387933e8341563260
Source dataset
uspto-grants-1998_07
Patent number
US05780480

Reaction notes

Loading…