Formic Acid → 2,4-Dichloro-5-Methylthio-6-Thiocyanopyrimidine

HRID 623240Notes

Reaction equation

HRID 623240 reaction equation
[CH3:1][S:2][C:3]1[C:4](Cl)=[N:5][C:6]([Cl:10])=[N:7][C:8]=1[Cl:9].C(O)=O.[S-:15][C:16]#[N:17].[K+]>O>[Cl:10][C:6]1[N:7]=[C:8]([Cl:9])[C:3]([S:2][CH3:1])=[C:4]([S:15][C:16]#[N:17])[N:5]=1

Participants

5

Reactant 3

HCID 284Formic AcidHCID 516872Potassium thiocyanateHCID 122255442,4,6-Trichloro-5-methylsulfanyl-pyrimidine

Product 1

HCID 136032642,4-Dichloro-5-Methylthio-6-ThiocyanopyrimidineYield 92.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

In a 50-ml four-necked flask equipped with a thermometer, reflux condenser and stirrer, were charged 2.30 g (0.010 mole) of 5-methylthio-2,4,6-trichloropyrimidine and 15 ml of formic acid. While stirring the contents at room temperature, 1.07 g (0.011 mole) of potassium thiocyanate was added. Then, the resulting mixture was heated and was then stirred at 50° C. for 1 hour. After cooling the reaction mixture, it was poured into a great deal of water. The precipitated solid was collected by filtration and dried to obtain 2.34 g of crude crystals (yield: 92.9%). A portion of the crude crystals was recrystallized from ethyl acetate, thereby obtaining a purified product. m.p. 143°-144.5° C.

Workup

  1. customIn a 50-ml four-necked flask equipped with a thermometer
  2. temperaturereflux condenser and stirrer
  3. temperatureThen, the resulting mixture was heated
  4. stirringwas then stirred at 50° C. for 1 hour
  5. temperatureAfter cooling the reaction mixture, it
  6. filtrationThe precipitated solid was collected by filtration
  7. customdried

Sources & evidence

ORD record
ord-beb9851e09c449ca850ab15f37199d4f
Source dataset
uspto-grants-1988_09
Patent number
US04774335

Reaction notes

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