Potassium Hydroxide → HCID 136464294, compound

HRID 2247850Notes

Reaction equation

HRID 2247850 reaction equation
[CH3:1][C:2]1[NH:7][C:6](=[S:8])[NH:5][C:4](=[O:9])[CH:3]=1.[OH-].[K+].[Cl-].Cl[CH2:14][C:15]1[CH:20]=[C:19]([O:21][CH3:22])[C:18]([CH2:23][CH3:24])=[CH:17][NH+:16]=1>O.[Cl-].C([N+](CCCC)(CCCC)CCCC)CCC.C(Cl)(Cl)Cl>[CH2:23]([C:18]1[C:19]([O:21][CH3:22])=[CH:20][C:15]([CH2:14][S:8][C:6]2[NH:5][C:4](=[O:9])[CH:3]=[C:2]([CH3:1])[N:7]=2)=[N:16][CH:17]=1)[CH3:24]

Participants

7

Reactant 3

HCID 14797Potassium HydroxideHCID 667493MethylthiouracilHCID 67946610HCID 67946610, compound

Product 1

HCID 136464294HCID 136464294, compoundYield 47%

Reagents, catalysts & solvents 3

HCID 70681Tetrabutylammonium ChlorideCatalystHCID 962WaterSolventHCID 6212ChloroformSolvent

Procedure

0.71 g (5 mmol) of 6-methyl-2-thiouracil and 0.65 g (11.7 mmol) of potassium hydroxide are dissolved in 10 ml of water. Simultaneously, 1.22 g (5.5 mmol) of 2-chloromethyl-5-ethyl-4-methoxypyridinium chloride (m.p.: 123°-125° C.) and 0.1 g of tetrabutylammonium chloride are dissolved in 10 ml of chloroform. After combining the two solutions the reaction mixture is vigorously stirred at room temperature for 20 hours. After separating the phases the aqueous layer is extracted 3 times with 5 ml of chloroform each, the combined organic phase is washed with sodium chloride solution, dried over anhydrous magnesium sulfate and evaporated under reduced pressure. The residue is thoroughly triturated with ethyl acetate, filtered and the crude product obtained is recrystallized from ethanol to obtain 0.68 g (47%) of the title compound in the form of white crystals, m.p.: 167°-168° C.

Workup

  1. customAfter separating the phases the aqueous layer
  2. extractionis extracted 3 times with 5 ml of chloroform each, the combined organic phase
  3. washis washed with sodium chloride solution
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customevaporated under reduced pressure
  6. customThe residue is thoroughly triturated with ethyl acetate
  7. filtrationfiltered
  8. customthe crude product obtained
  9. customis recrystallized from ethanol

Sources & evidence

ORD record
ord-517fc6150db64ae79af94e1b3c22acf6
Source dataset
uspto-grants-1991_08
Patent number
US05037830

Reaction notes

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