Sodium Bicarbonate → Mdl 19660

HRID 2254636Notes

Reaction equation

HRID 2254636 reaction equation
[Cl:1][C:2]1[CH:16]=[CH:15][C:5]([C:6]([NH:8][N:9]([CH3:14])[C:10]([NH:12][CH3:13])=[S:11])=O)=[CH:4][CH:3]=1.Cl.N1C=CC=CC=1.C([O-])(O)=O.[Na+]>>[Cl:1][C:2]1[CH:16]=[CH:15][C:5]([C:6]2[N:12]([CH3:13])[C:10](=[S:11])[N:9]([CH3:14])[N:8]=2)=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 516892Sodium BicarbonateHCID 10176127Pyridinium chlorideHCID 14257817HCID 14257817, compound

Product 1

HCID 163824Mdl 19660

Procedure

The 1:1 mixture of 1-(4-chlorobenzoyl)-2,4-dimethylthiosemicarbazide and pyridine hydrochloride (3.61 g of mixture) from Example 2 and 1 molar aqueous NaHCO3 (100 ml, 1.00×10-1 mole) were stirred and warmed to reflux. After refluxing for 5 hours the reaction was allowed to cool. It was then placed in a refrigerator for several hours before the precipitate was collected by filtration. The collected material was dried partially by suction before being transferred to a desiccator where it was dried at high vacuum. This affords the desired product as a beige powder: 2.01 g (84%). This was purified by flash chromatography and subsequent crystallization from isopropanol yielding small, slightly yellowish plates: 1.74 g (73%), mp 113°-115° C.

Workup

  1. temperaturewarmed to reflux
  2. temperatureAfter refluxing for 5 hours the reaction
  3. temperatureto cool
  4. waitIt was then placed in a refrigerator for several hours before the precipitate
  5. filtrationwas collected by filtration
  6. customThe collected material was dried partially by suction
  7. custombefore being transferred to a desiccator
  8. customwhere it was dried at high vacuum

Sources & evidence

ORD record
ord-35df994ba4904c1b83cb2bf953be6303
Source dataset
uspto-grants-1993_08
Patent number
US05236942

Reaction notes

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