Potassium Carbonate → HCID 10498867, compound

HRID 1291039Notes

Reaction equation

HRID 1291039 reaction equation
[NH2:1][C:2]([NH2:19])=[N:3][C:4](=[O:18])[C:5]1[CH:10]=[C:9]([S:11]([CH3:14])(=[O:13])=[O:12])[C:8](Cl)=[CH:7][C:6]=1[CH2:16][CH3:17].C([O-])([O-])=O.[K+].[K+].C[Si](C)(C)[O:28][C:29]1[CH:34]=[CH:33][N:32]=[CH:31][CH:30]=1>>[NH2:1][C:2]([NH2:19])=[N:3][C:4](=[O:18])[C:5]1[CH:10]=[C:9]([S:11]([CH3:14])(=[O:13])=[O:12])[C:8]([N:32]2[CH:33]=[CH:34][C:29](=[O:28])[CH:30]=[CH:31]2)=[CH:7][C:6]=1[CH2:16][CH3:17]

Participants

4

Reactant 3

HCID 11430Potassium CarbonateHCID 10566392HCID 10566392, compoundHCID 131625554-[(Trimethylsilyl)oxy]pyridine

Product 1

HCID 10498867HCID 10498867, compound

Procedure

3 g of N-diaminomethylene-2-ethyl-4-chloro-5-methylsulfonylbenzamide [obtainable by reacting methyl 2-methyl-4-chloro-5-methylsulfonylbenzoate with guanidine] are heated with 30 ml of 4-trimethylsilyloxypyridine in the presence of 3 g of K2CO3 in a closed tube at 135° for five hours. The mixture is cooled, the excess silylpyridine is removed by decanting, and the residue is triturated with ether and filtered off with suction. The solid residue is then dissolved in methanol and chromatographed over silica gel (ethyl acetate/methanol). Recrystallization from isopropanol and ethanol gives N-diaminomethylene-2-ethyl-4-(1,4-dihydro-4-oxo-1-pyridyl)-5-methylsulfonylbenzamide, m.p. 261-263°.

Workup

  1. temperatureThe mixture is cooled
  2. customthe excess silylpyridine is removed
  3. customby decanting
  4. customthe residue is triturated with ether
  5. filtrationfiltered off with suction
  6. dissolutionThe solid residue is then dissolved in methanol
  7. customchromatographed over silica gel (ethyl acetate/methanol)
  8. customRecrystallization from isopropanol and ethanol

Sources & evidence

ORD record
ord-53e34f0f70fb438d953ee238ef87666e
Source dataset
uspto-grants-1998_05
Patent number
US05753680

Reaction notes

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