Hydrochloric Acid → HCID 22939285, compound

HRID 499275Notes

Reaction equation

HRID 499275 reaction equation
N[C:2]1[C:10]([CH3:11])=[CH:9][C:8]([CH3:12])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[OH-].[Na+].N([O-])=O.[Na+].Cl.C([O-])(=O)C.[K+].CCOC([S-])=[S:29].[K+]>O>[SH:29][C:2]1[C:10]([CH3:11])=[CH:9][C:8]([CH3:12])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5]

Participants

8

Reactant 6

HCID 313Hydrochloric Acid2×HCID 14798Sodium HydroxideHCID 2598342-Amino-3,5-dimethylbenzoic acidHCID 517044Potassium AcetateHCID 2735045Potassium ethylxanthateHCID 23668193Sodium Nitrite

Product 1

HCID 22939285HCID 22939285, compoundYield 58.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

A mixture of 2-amino-3,5-dimethylbenzoic acid (5.6 g, 33.9 mmol), sodium hydroxide (1.5 g, 37.5 mmol), sodium nitrite (2.3 g, 34.0 mmol) and water (40 ml) was added dropwise to a mixture of concentrated hydrochloric acid (10 ml) and ice (10 g) under cooling with ice while adding ice in order to keep the reaction temperature under 5° C. The reaction mixture was stirred under ice-cooling condition for 30 minutes, neutralized with potassium acetate and added to a solution of potassium o-ethyl dithiocarbonate (16.9 g, 105.4 mmol) in water (50 ml) at 80° C. After stirring at the same temperature for 20 minutes, the reaction mixture was acidified (pH 3) by use of concentrated hydrochloric acid. The water layer was separated. 10% aqueous sodium hydroxide solution (30 ml) was added to the oily substance and the mixture was stirred at 80° C. for 2 hrs. Furthermore, sodium hydrogen sulfite (4.0 g) was added to the mixture, and the mixture was stirred at the same temperature for 10 minutes. The reaction mixture was filtered and the filtrate was acidified (about pH 4) by use of concentrated hydrochloric acid. The precipitate was collected by filtration and dissolved in a mixture of methanol (5 ml) and diisopropylether (80 ml), dried and concentrated under reduced pressure to give the titled compound as crystals (3.6 g, 58%).

Workup

  1. temperatureunder cooling with ice
  2. additionwhile adding ice in order
  3. customunder 5° C
  4. temperaturecooling condition for 30 minutes
  5. stirringAfter stirring at the same temperature for 20 minutes
  6. customThe water layer was separated
  7. addition10% aqueous sodium hydroxide solution (30 ml) was added to the oily substance
  8. stirringthe mixture was stirred at 80° C. for 2 hrs
  9. additionFurthermore, sodium hydrogen sulfite (4.0 g) was added to the mixture
  10. stirringthe mixture was stirred at the same temperature for 10 minutes
  11. filtrationThe reaction mixture was filtered
  12. filtrationThe precipitate was collected by filtration
  13. dissolutiondissolved in a mixture of methanol (5 ml) and diisopropylether (80 ml)
  14. customdried
  15. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-b4d6b4e4d9254bc4b06e9ed243c027b5
Source dataset
uspto-grants-2010_08
Patent number
US07767665B2

Reaction notes

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